1-Substituted 4-carbamoyl-1,2,4-triazol-5-one derivatives and herbicide

ABSTRACT

A 1-phenyl, naphthyl or aralkyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-one derivative represented by the general formula (I) ##STR1## wherein A is an unsubstituted or substituted phenyl group, 1-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group or an aralkyl group such as an unsubstituted or substituted benzyl group and so on, R 1  is a lower alkyl group and so on, and R 2  is an unsubstituted or substituted phenyl group and so on, was prepared as novel compounds. This 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative does not substantially exhibit phytotoxicity to various agricultural crop plants and therefore is useful as a selective herbicide.

This application is a 371 of PCT/JP98/00803 filed Feb. 26, 1998.

TECHNICAL FIELD

This invention relates to a new1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative useful as aherbicide, and also this invention relates to a herbicidal compositioncomprising said derivative as an active ingredient. This invention istherefore useful in the fields of chemical industry and agriculture,especially in the field of the art for the manufacture of agriculturalchemicals.

BACKGROUND ART

Hitherto, it has already been known that certain 1,2,4-triazol-5-onederivatives and tetrazolinone derivatives have herbicidal and fungicidalactivities, as described below.

For example, the known 1,2,4-triazol-5-one derivatives include suchcompounds as described in literatures (1) to (4) below.

(1) Japanese patent application first publication (Kokai) No.Hei-7-76578 describes a compound represented by the general formula (A)##STR2## wherein X denotes oxygen atom or sulfur atom, R₁ denotes ahaloalkyl group, R₂ denotes a cycloalkyl group, a cycloalkylalkyl groupand so on, R₃ denotes hydrogen atom or a halogen atom, R₄ denotesnitrile group or nitro group and R₅ denotes a halogen atom or aheterocyclic alkoxy group and so on.

(2) Japanese patent application first publication (Kokai) No.Hei-3-106865 describes a compound represented by the general formula (B)##STR3## wherein R₁ denotes a cycloalkyl group, a phenylalkyl group, ahalogen atom, an aminocarbonyl group substituted with a substitutedphenyl group, and so on; R₂ denotes hydrogen atom or a lower alkylgroup; and R₃ denotes a halogen atom, an alkyl group and so on.

(3) Japanese patent application first publication (Kokai) No.Sho-64-29368 describes a compound represented by the general formula (C)##STR4## wherein X and Y denote oxygen atom or sulfur atom, R₁ denoteshydrogen atom and so on, R₂ denotes an unsubstituted or substitutedphenyl group, an aralkyl group and so on, and R₃ and R₄ denote hydrogenatom, an alkyl group or an unsubstituted or substituted aryl group andso on.

(4) Japanese patent application first publication (Kokai) No.Hei-6-293744 describes a compound represented by the general formula (D)##STR5## wherein R₁ denotes hydrogen atom and so on; R₂ denotes ##STR6##in which R₆ and R₇ denote an alkyl group, an alkenyl group, an alkynylgroup, a cycloalkyl group, an aryl group and so on; R₃ denotes hydrogenatom, an alkyl group, a haloalkyl group and so on; R₄ denotes hydrogenatom and so on; and R₅ denotes amino group or hydroxy group and so on.

Furthermore, various 1,2,4-triazol-5-one derivatives have been describedin the following literatures (5) to (24), namely (5) Japanese patentapplication first publication (Kokai) No. Sho-56-32403; (6) Japanesepatent application first publication (Kokai) No. Sho-56-53663; (7)Japanese patent application first publication (Kokai) No. Sho-56-53662;(8) Japanese patent application first publication (Kokai) No.Sho-58-23680; (9) U.S. Pat. No. 4,705,557; (10) PCT internationalpublication No. WO85/01637; (11) PCT international publication No.WO86/02642; (12) U.K. patent No. 2230261 specification; (13) Japanesepatent application first publication (Kokai) No. Hei-3-106865; (14)German patent No. 4437049; (15) German patent No.4435476; (16) Germanpatent No. 4431219; (17) U.S. Pat. No. 5,035,740 specification ; (18)Japanese patent application first publication (Kokai) No. Hei-3-181472;(19) German patent No. 3920414; (20) Japanese patent application firstpublication (Kokai) No. Hei-3-17070; (21) South African patent No.8805308; (22) Japanese patent application first publication (Kokai) No.Sho-64-29368; (23) Japanese patent application first publication (Kokai)No. Sho-63-255271; and (24) Japanese patent application firstpublication (Kokai) No. Sho-52-118471.

However, the above-mentioned literatures (1) to (24) do not describe any1,2,4-triazol-5-one derivatives having carbamoyl group at the 4-positionthereof.

Furthermore, for the tetrazolinone derivatives there have been knownsuch compounds as described in literatures (25) to (50) below.

(25) Japanese patent application first publication (Kokai) No.Sho-62-12767 describes a compound represented by the general formula (E)##STR7## wherein R denotes a cycloalkyl group, phenyl group, naphthylgroup and so on, R₁ and R₂ may be the same or different and each denotea C₁ -C₆ alkyl group, a C₅ -C₆ alkenyl group, a C₅ -C₆ cycloalkyl group,a C₇ -C₉ aralkyl group, or phenyl group which may be substituted with aC₁ -C₆ alkyl group, a C₁ -C₆ haloalkyl group or a C₁ -C₆ alkoxy groupand so on.

In addition, the known tetrazolinone derivatives include such compoundsas described in (26) Japanese patent application first publication(Kokai) No. Sho-60-146879; (27) Japanese patent application firstpublication (Kokai) No. Hei-5-331154; (28) Japanese patent applicationfirst publication (Kokai) No. Hei-5-339249; (29) Japanese patentapplication first publication (Kokai) No. Hei-5-331153; (30) Japanesepatent application first publication (Kokai) No. Hei-6-306061; (31)Japanese patent application first publication (Kokai) No. Hei-6-199818;(32) Japanese patent application first publication (Kokai) No.Hei-7-258230; (33) Japanese patent application first publication (Kokai)No. Hei-8-81459; (34) Japanese patent application first publication(Kokai) No. Hei-8-99975; (35) Japanese patent application firstpublication (Kokai) No. Hei-8-119947; (36) Japanese patent applicationfirst publication (Kokai) No. Hei-8-119948; (37) Japanese patentapplication first publication (Kokai) No. Hei-8-119950; (38) Japanesepatent application first publication (Kokai) No. Hei-8-119951; (39)Japanese patent application first publication (Kokai) No. Hei-8-225547;(40) Japanese patent application first publication (Kokai) No.Hei-8-311048; (41) Japanese patent application first publication (Kokai)No. Hei-8-259549;

(42) U.S. Pat. No. 4,830,661 specification; (43) U.S. Pat. No. 4,956,469specification; (44) U.S. Pat. No. 5,003,075 specification; (45) U.S.Pat. No. 5,019,152 specification; (46) Portuguese patent No. 101563specification; (47) Japanese patent application first publication(Kokai) No. Hei-8-119949; (48) Japanese patent application firstpublication (Kokai) No. Hei-8-259548; (49) U.S. Pat. No. 5,136,868specification; and (50) PCT international publication No. WO85/01939.

In the development of the herbicide, it is an important subject tocreate such new herbicidal compounds which exhibit a selectiveherbicidal activity owing to that some differences occur between thesensitivity of crop plants, namely useful cultivated plants and thesensitivity of weeds against a herbicide, and so on. However, whencertain herbicidal compounds exhibit a phytotoxicity to the crop plantseven if they have a high herbicidal activity, it is hard to say thatsuch herbicidal compounds can be used satisfactorily as the herbicide inpractice. Thus, it is now demanded to develop such new herbicidalcompounds which is free from the drawbacks mentioned above. In thisview, the above-mentioned 1,2,4-triazol-5-one and tetrazolinonederivatives which are known compounds are not necessarily a satisfactoryherbicide. Accordingly, it is an object of this invention to provide, inplace of the above-mentioned known herbicidal compounds, such new1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives which have anexcellent herbicidal activity and show very low phytotoxicity to thecrop plants and hence have a safety to the crop plants when used as theherbicide. It is another object of this invention to provide a herbicidecomprising such new 1-substituted-4-carbamoyl-1,2,4-triazol-5-onederivatives as an active ingredient.

DISCLOSURE OF INVENTION

In order to achieve the above-mentioned objects of this invention, we,the present inventors, have eagerly studied on 1,2,4-triazol-5-onederivatives. As a result, the present inventors have now succeeded insynthesizing a number of new1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives which havehitherto been unknown. Furthermore, the present inventors have eagerlyresearched herbicidal activity and utilities of said new1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives sosynthesized. As a result, the present inventors have surprisingly foundthat a new 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivativerepresented by the general formula (I) given below does not show anyphytotoxicity to the useful cultivated plants, namely crop plants anddoes exhibit an excellent herbicidal activity against them even at a lowapplication rate thereof. According to such our findings, the presentinventors have now completed the present inventions.

According to a first aspect of this invention, therefore, there isprovided a 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivativerepresented by the general formula (I) ##STR8## wherein: (i) A is anunsubstituted or substituted phenyl group represented by the formula##STR9## in which X may be the same or different and is a halogen atom,a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, alower haloalkoxy group, cyano group, nitro group, methylthio group,methylsulfinyl group, methylsulfonyl group, phenoxy group, acetylaminogroup or trifluoroacetylamino group, and n is 0 or an integer of 1 to 5,or

(ii) A is 1-naphthyl group of the formula ##STR10## or5,6,7,8-tetrahydro-1-naphthyl group of the formula ##STR11## (iii) A isan unsubstituted or substituted benzyl group or phenethyl grouprepresented by the formula ##STR12## in which X and n have the samemeanings as defined above, R₃ is hydrogen atom or methyl group and kdenotes an integer of 1 to 2;

R₁ is a lower alkyl group, a lower alkenyl group, a lower alkynyl groupor a lower cycloalkyl group; and

R₂ is a lower alkyl group, a lower cycloalkyl group or an unsubstitutedor substituted phenyl group having the formula ##STR13## in which m is 0or an integer of 1 to 5 and Y may be the same or different and is ahalogen atom, a lower alkyl group, a lower haloalkyl group, a loweralkoxy group, a lower haloalkoxy group or cyano group; or R₂ is a benzylgroup of which benzene ring may be substituted with a halogen atom; orR₂ is an unsubstituted or substituted pyridyl group having the formula##STR14## in which Z is hydrogen atom or chlorine atom.

The new 1,2,4-triazol-5-one derivative represented by the generalformula (I) according to the first aspect of this invention has acharacteristic chemical structure in that the 1-position of the1,2,4-triazol-5-one ring is substituted by an unsubstituted orsubstituted phenyl group, 1-naphthyl group or an aralkyl group and alsothat the 4-position of said ring is substituted by an N,N-di-substitutedcarbamoyl group.

With the derivative of the general formula (I) above, the term "a loweralkyl group" used for the definitions of R₁, R₂, X and Y means astraight-chain or branched-chain alkyl group having 1 to 6 carbon atoms,such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl,t-butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, n-hexyl,4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl,1,1-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethylbutyl,1-ethyl-2-methyl-propyl, 1-methyl-1-ethypropyl, 1-methyl-2-ethylpropyl,2-methyl-1-ethylpropyl or 2-methyl-2-ethylpropyl group.

The term "a lower alkenyl group" used for the definition of R₁ given inthe general formula (I) means a straight-chain or branched-chain alkynylgroup having 3 to 6 carbon atoms, such as vinyl, 1-propenyl, 2-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-ethyl-2-propenyl, 2-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-ethyl-2-butenyl, 3-butenyl,2-pentenyl, 3-pentenyl, 4-pentenyl, 2-hexenyl, 3-hexenyl or 4-hexenylgroup.

The term "a lower alkynyl group" used for the definition of R₁ given inthe general formula (I) means a straight-chain or branched-chain alkenylgroup having 3 to 6 carbon atoms, such as 2-propynyl,1-methyl-2-propynyl, 2-butynyl, 1-methyl-2-butynyl, 1-ethyl-2-butynyl,3-butynyl, 2-methyl-3-butynyl, 2-pentynyl, 4-pentynyl, 2-hexynyl,3-hexynyl, 4-hexynyl or 5-hexynyl group.

The term "a cycloalkyl group" used for the definitions of R₁ and R₂given in the general formula (I) means a cycloalkyl group having 3 to 7carbon atoms which may have a branched-chain and which maybe, forexample, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,2-methylcyclopropyl, 2-methylcyclopentyl or 2-methylcyclohexyl group.

The halogen atom set forth in the definitions of X and Y given in thegeneral formula (I) means chlorine, bromine, fluorine or iodine atom.

The term "a lower haloalkyl group" used for the definitions of X and Ygiven in the general formula (I) means a lower alkyl group having assubstituent(s) one or more of halogen atoms such as chlorine, bromine,fluorine or iodine atom, which maybe, for example, trifluoromethyl,chloromethyl, bromomethyl, dichloromethyl, difluoromethyl,trichloromethyl, 2-chloroethyl, 2-bromoethyl, 1,1-difluorethyl,2,2,2-trifluoroethyl, 3-chloropropyl or 3-iodopropyl group.

The term "a lower alkoxy group" used for the definitions of X and Ygiven in the general formula (I) means a straight-chain orbranched-chain alkoxy group having 1 to 6 carbon atoms, such as methoxy,ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy,n-pentyloxy, isopentyloxy or n-hexyloxy group.

The term "a lower haloalkoxy group" used for the definitions of X and Ygiven in the general formula (I) means a haloalkoxy group having 1 to 6carbon atoms, such as difluoromethoxy, trifluoromethoxy and2,2,2-trifluoroethoxy group.

The term "benzyl group of which benzene ring may be substituted with ahalogen atom", which is used for the definition of R₂ given in thegeneral formula (I), means benzyl group, or a halo-benzyl group such as2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group,2-fluorobenzyl group, 3-fluorobenzyl group or 4-fluorobenzyl group.

The term "unsubstituted or substituted pyridyl group" used for thedefinition of R₂ given in the general formula (I) means, for example,2-pyridyl group, 4-pyridyl group, 5-chloro-2-pyridyl group and others.

The 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative representedby the general formula (I) may preferably be such a1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (I) wherein R₁ is a lower alkyl group, R₂ is a mono-halo ordi-halo-substituted phenyl group, X is a halogen atom, a lower alkylgroup or a lower haloalkyl group and n is 0 or an integer of 1 to 2.Also, said derivative may preferably be such a1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (I) wherein R₁ is a lower alkyl group, R₂ is a lower cycloalkylgroup, X is a halogen atom, a lower alkyl group or a lower haloalkylgroup and n is 0 or an integer of 1 to 2.

Further, the derivative of the formula (I) may preferably be such a1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (I) wherein R₁ is isopropyl group, R₂ is a mono-halo-substitutedor difluoro-substituted phenyl group, X is a halogen atom or a loweralkyl group and n is 0 or an integer of 1 to 2.

The 1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative representedby the general formula (I) according to the first aspect of thisinvention may be classified broadly into the following three classes ofthe derivatives, namely the derivatives having the following generalformulae (Ia), (Ib) and (Ic), respectively.

(1) A 1-phenyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative represented by the general formula (Ia) ##STR15## wherein: Xhas the same meaning as defined in the general formula (I), namely X maybe the same or different and is a halogen atom, a lower alkyl group, alower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group,cyano group, nitro group, methylthio group, methylsulfinyl group,methylsulfonyl group, phenoxy group, acetylamino group ortrifluoroacetylamino group;

n is 0 or an integer of 1 to 5; and

R₁ and R₂ have the same meanings as defined in the general formula (I),namely R₁ is a lower alkyl group, a lower alkenyl group, a lower alkynylgroup or a lower cycloalkyl group, and R₂ is a lower alkyl group, alower cycloalkyl group or an unsubstituted or substituted phenyl grouphaving the formula ##STR16## in which m is 0 or an integer of 1 to 5 andY may be the same or different and is a halogen atom, a lower alkylgroup, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxygroup or cyano group; or R₂ is a benzyl group of which benzene ring maybe substituted with halogen atom(s); or R₂ is an unsubstituted orsubstituted pyridyl group having the formula ##STR17## in which Z is ahydrogen atom or chlorine atom; (2) A 1-naphthyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative represented by the generalformula (Ib) ##STR18## in which: A^(a) is 1-naphthyl group of theformula ##STR19## or 5,6,7,8-tetrahydrol-naphthyl group of the formula##STR20## ,and R₁ and R₂ have the same meanings as defined in thegeneral formula (I), namely R₁ is a lower alkyl group, a lower alkenylgroup, a lower alkynyl group or a lower cycloalkyl group, and R₂ is alower alkyl group, a lower cycloalkyl group or an unsubstituted orsubstituted phenyl group having the formula ##STR21## in which m is 0 oran integer of 1 to 5 and Y may be the same or different and is a halogenatom, a lower alkyl group, a lower haloalkyl group, a lower alkoxygroup, a lower haloalkoxy group or cyano group; or R₂ is a benzyl groupof which benzene ring may be substituted with a halogen atom; or R₂ isan unsubstituted or substituted pyridyl group having the formula##STR22## in which Z is a hydrogen atom or chlorine atom; and (3) A1-aralkyl-4-(N,N-disubstituted carbamoyl)-1,2,4-triazol-5-one derivativerepresented by the general formula (Ic) ##STR23## in which: X has thesame meaning as defined in the general formula (I), namely X may be thesame or different and is a halogen atom, a lower alkyl group, a lowerhaloalkyl group, a lower alkoxy group, a lower haloalkoxy group, cyanogroup, nitro group, methylthio group, methylsulfinyl group,methylsulfonyl group, phenoxy group, acetylamino group ortrifluoroacetylamino group;

n is 0 or an integer of 1 to 5;

R₁ and R₂ have the same meanings as defined in the general formula (I),namely R₁ is a lower alkyl group, a lower alkenyl group, a lower alkynylgroup or a lower cycloalkyl group, and R₂ is a lower alkyl group, alower cycloalkyl group or an unsubstituted or substituted phenyl grouphaving the formula ##STR24## in which m is 0 or an integer of 1 to 5 andY may be the same or different and is a halogen atom, a lower alkylgroup, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxygroup or cyano group; or R₂ is a benzyl group of which benzene ring maybe substituted with halogen atom(s); or R₂ is an unsubstituted orsubstituted pyridyl group having the formula ##STR25## in which Z is ahydrogen atom or chlorine atom; R₃ is a hydrogen atom or methyl group;and

k is an integer of 1 or 2.

The derivative of the general formula (Ia) above may preferably be sucha 1-phenyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative represented by the general formula (Ia-1) ##STR26## whereR_(1a) is a lower alkyl group, R_(2a) is a mono-halo- ordi-halo-substituted phenyl group, X^(a) is a halogen atom, a lower alkylgroup or a lower haloalkyl group, and n is 0 or an integer of 1 to 2.

In addition, the derivative of the general formula (Ia) may preferablybe such a 1-phenyl-4-(N,N-di-substituted carbamoyl) -1,2,4-triazol-5-onederivative represented by the general formula (Ia-1-1) ##STR27## wherei-Pr means isopropyl group, R_(2a) is a mono-halo- ordi-halo-substituted phenyl group, X^(a) is a halogen atom, a lower alkylgroup or a lower haloalkyl group, and n is 0 or an integer of 1 to 2.

Furthermore, the derivative of the general formula (Ia-1-1) may be a1-phenyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-one derivativerepresented by the general formula (Ia-1-2) ##STR28## where i-Pr meansisopropyl group, T is hydrogen atom or fluorine atom, X^(b) may be thesame or different and is chlorine atom, bromine atom, fluorine atom,methyl group, ethyl group or trifluoromethyl group, and n is 0 or aninteger of 1 to 2.

Representative particular examples of the 1-phenyl-4-(N,N-di-substitutedcarbamoyl) -1,2, 4-triazol-5-one derivative of the general formula(Ia-1-2), which is embraced in the derivative of the general formula (I)according to the first aspect of this invention, are particularcompounds shown in Table 1a given hereinafter. Some of the preferredexemplary compounds include a class of compounds listed below:

(1) 1-phenyl-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.4 or No.8in Table 1a given hereinafter),

(2) 1-(2-chlorophenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.38 orNo.35 in Table 1a given hereinafter),

(3) 1-(3-chlorophenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.75 orNo.76 in Table 1a given hereinafter),

(4) 1-(2-fluorophenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.165 orNo.166 in Table 1a given hereinafter),

(5) 1-(2,4-difluorophenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.184 orNo.181 in Table 1a given hereinafter),

(6) 1-(2-fluoro-4-chlorophenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.322 inTable 1a given hereinafter),

(7) 1-(2-methylphenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.332 orNo.331 in Table 1a given hereinafter),

(8) 1-(2,3-dimethylphenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.581 orNo.582 in Table 1a given hereinafter), or

(9) 1-(2-chloro-4-methylphenyl)-4-(N-isopropyl-N-4-fluoro or2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one (Compound No.634 orNo.633 in Table 1a given hereinafter).

In addition, further examples of the preferred compounds include alsocompounds of Compound Nos.231, 234, 369, 270, 281, 284, 576, 577, 587,591, 592, 596, 597, 635, 636, 637, 638, 639 and 640 shown in thefollowing Table 1a.

Furthermore, the 1-phenyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative of the general formula (Ia)may preferably be such a 1-phenyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative represented by the generalformula (Ia-2) ##STR29## where X and n have the same meanings as definedin the general formula (I) or (Ia), R_(1b) is a lower alkyl group, andR_(2b) is a lower cycloalkyl group.

In particular, the derivative of the general formula (Ia-2) maypreferably be a 1-phenyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative of the above general formula(Ia-2) where X is chlorine atom, fluorine atom, methyl group, ethylgroup, trifluoromethyl group or trifluoromethyloxy group, n is 0 or aninteger of 1 to 2, R_(1b) is methyl group, ethyl group, n-propyl groupor isopropyl group, and R_(2b) is cyclopropyl group , cyclopentyl groupor cyclohexyl group.

The 1-naphthyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative of the general formula (Ib) given hereinbefore is preferablysuch derivative of the general formula (Ib) where R₁ is a lower alkylgroup, particularly isopropyl group, and R₂ is monohalo ordihalo-substituted phenyl group, particularly 4-fluoro or2,4-difluorophenyl group, and n is 0 or an integer of 1 to 2.

Representative particular examples of the derivative of the generalformula (Ib) include compounds of Compound Nos.649 to 652 shown in Table1b given hereinafter. Particularly preferred compound is1-(5,6,7,8-tetrahydro-1-naphthyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one(Compound No.650).

The 1-aralkyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative of the general formula (Ic) shown hereinbefore according tothe first aspect of this invention may preferably be a1-aralkyl-4-(N,N-di-substituted carbamoyl) -1,2,4-triazol-5-onederivative represented by the general formula (Ic-1) ##STR30## whereR_(1a) is a lower alkyl group, R_(2a) is a mono-halo- ordi-halo-substituted phenyl group, X^(a) is a halogen atom, a lower alkylgroup or a lower haloalkyl group, n is 0 or an integer of 1 to 2 and kis an integer of 1 or 2.

Particularly preferred derivative of the general formula (Ic-1) is a1-aralkyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative represented by the general formula (Ic-1-1) ##STR31## inwhich i-Pr means isopropyl group, T is hydrogen atom or fluorine atom,X^(b) may be the same or different and is chlorine atom, bromine atom,fluorine atom, methyl group, ethyl group or trifluoromethyl group, n is0 or an integer of 1 to 2, R₃ is hydrogen atom or methyl group and k isan integer of 1 or 2.

Representative examples of the 1-aralkyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative of the general formula (Ic)include compounds of Compound Nos.653 to 684 shown in Table 1c givenhereinafter. Particularly preferred compounds among them are1-(2,3-dichlorobenzyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one(Compound No.662) and1-(2-chloro-a-methylbenzyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one(Compound No.675).

According to a second aspect of this invention, there is provided aherbicidal composition comprising as an active ingredient the1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative represented bythe general formula (I) ##STR32## wherein A, R₁ and R₂ have the samemeanings as defined above.

The herbicidal composition of the second aspect of this invention maycontain as the active ingredient the1-phenyl-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (Ia) as defined above. Furthermore, the herbicidal compositionalso may contain as the active ingredient the1-naphthyl-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (Ib) as defined above.

Besides, the herbicidal composition of the second aspect of thisinvention also may contain as the active ingredient the1-aralkyl-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (Ic) as defined above.

BEST MODE FOR CARRYING OUT THE INVENTION

Next, representative particular examples of the1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (Ia) according to the first aspect of this invention are shownin Table 1a given hereinafter. In addition, representative particularexamples of the 1-naphthyl-4-(N,N-disubstitutedcarbamoyl)-I,2,4-triazol-5-one derivative of the general formula (Ib)are shown in Table 1b given hereinafter, and representative examples ofthe 1-aralkyl-4-(N,N-disubstituted carbamoyl)-1,2,4-triazol-5-onederivative of the general formula (Ic) are shown in Table 1c givenhereinafter.

Compound Nos. given in these Table 1a, Table 1b and Table 1c arereferred to also in Examples and Test Examples given after.

In Table 1a, such compounds where Xn is shown as H indicate that thephenyl group exhibited in the formula (I) does not have the substituent(X), namely such compounds where n=0. Furthermore, in Table 1a to Table1c, Me denotes methyl group, Et denotes ethyl group, Pr denotes propylgroup and Bu denotes butyl group. For instance, i-Pr denotes isopropylgroup, n-Pr denotes n-propyl group, i-Bu denotes i-butyl group, n-Budenotes n-butyl group and sec-Bu denotes secondary butyl group.

                                      TABLE 1a                                    __________________________________________________________________________    General formula (Ia)                                                           ##STR33##                                                                    Compound No.                                                                         X.sub.n     R.sub.1  R.sub.2       Physical data                       __________________________________________________________________________    1      H           i-Pr                                                                                    ##STR34##    mp 144-145° C.               2      H           i-Pr                                                                                    ##STR35##                                        3      H           i-Pr                                                                                    ##STR36##                                        4      H           i-Pr                                                                                    ##STR37##    mp 142-143° C.               5      H           i-Pr                                                                                    ##STR38##                                        6      H           i-Pr                                                                                    ##STR39##                                        7      H           i-Pr                                                                                    ##STR40##                                        8      H           i-Pr                                                                                    ##STR41##    mp 104-106° C.               9      H           i-Pr                                                                                    ##STR42##                                        10     H           i-Pr                                                                                    ##STR43##                                        11     H           i-Pr                                                                                    ##STR44##                                        12     H           i-Pr                                                                                    ##STR45##                                        13     H           i-Pr     i-Pr          mp 174-175° C.               14     H           i-Pr                                                                                    ##STR46##    mp 136-137° C.               15     H           Et       Et                                                16     H           Et                                                                                      ##STR47##    mp 123-124° C.               17     H           n-Pr                                                                                    ##STR48##    mp 79-80° C.                 18     H           --CH.sub.2 CH═CH.sub.2                                                              ##STR49##    mp 101-102° C.               19     H           --CH.sub.2 C.tbd.CH                                                                     ##STR50##                                        20     H           i-Bu                                                                                    ##STR51##                                        21     H           i-Pr                                                                                    ##STR52##                                        22     H           i-Pr                                                                                    ##STR53##                                        23     H           i-Pr                                                                                    ##STR54##                                        24     H           i-Pr                                                                                    ##STR55##                                        25     2-Cl        Me                                                                                      ##STR56##    mp 141-143° C.               26     2-Cl        Et                                                                                      ##STR57##    mp 110-111° C.               27     2-Cl        n-Pr                                                                                    ##STR58##    mp 94-95° C.                 28     2-Cl        n-Bu                                                                                    ##STR59##    mp 90-91° C.                 29     2-Cl        i-Bu                                                                                    ##STR60##    mp 112-114° C.               30     2-Cl        sec-Bu                                                                                  ##STR61##    mp 88-89° C.                 31     2-Cl                                                                                       ##STR62##                                                                              ##STR63##    mp 90-91° C.                 32     2-Cl        --CH.sub.2 CH═CH.sub.2                                                              ##STR64##    mp 105-106° C.               33     2-Cl        --CH.sub.2 C.tbd.CH                                                                     ##STR65##    mp 97-99° C.                 34     2-Cl        i-Pr                                                                                    ##STR66##    mp 132-134° C.               35     2-Cl        i-Pr                                                                                    ##STR67##    mp 146-147° C.               36     2-Cl        i-Pr                                                                                    ##STR68##    mp 106-168° C.               37     2-Cl        i-Pr                                                                                    ##STR69##                                        38     2-Cl        i-Pr                                                                                    ##STR70##    mp 118-120° C.               39     2-Cl        i-Pr                                                                                    ##STR71##    mp 125-127° C.               40     2-Cl        i-Pr                                                                                    ##STR72##    mp 134-135° C.               41     2-Cl        i-Pr                                                                                    ##STR73##    mp 154-156° C.               42     2-Cl        i-Pr                                                                                    ##STR74##    mp 187-189° C.               43     2-Cl        i-Pr                                                                                    ##STR75##                                        44     2-Cl        i-Pr                                                                                    ##STR76##    mp 164-166° C.               45     2-Cl        i-Pr                                                                                    ##STR77##    mp 80-82° C.                 46     2-Cl        i-Pr                                                                                    ##STR78##                                        47     2-Cl        i-Pr                                                                                    ##STR79##                                        48     2-Cl        i-Pr                                                                                    ##STR80##                                        49     2-Cl        i-Pr                                                                                    ##STR81##                                        50     2-Cl        i-Pr                                                                                    ##STR82##                                        51     2-Cl        i-Pr                                                                                    ##STR83##                                        52     2-Cl        i-Pr                                                                                    ##STR84##                                        53     2-Cl        i-Pr                                                                                    ##STR85##                                        54     2-Cl        i-Pr                                                                                    ##STR86##    mp 114-116° C.               55     2-Cl        i-Pr                                                                                    ##STR87##                                        56     2-Cl        i-Pr                                                                                    ##STR88##                                        57     2-Cl        i-Pr                                                                                    ##STR89##                                        58     2-Cl        i-Pr                                                                                    ##STR90##                                        59     2-Cl        i-Pr                                                                                    ##STR91##                                        60     2-Cl        i-Pr                                                                                    ##STR92##                                        61     2-Cl        i-Pr                                                                                    ##STR93##                                        62     2-Cl        n-Pr                                                                                    ##STR94##    n.sub.D.sup.18 1.5556               63     2-Cl                                                                                       ##STR95##                                                                             Et            n.sub.D.sup.18 1.5558               64     2-Cl                                                                                       ##STR96##                                                                              ##STR97##                                        65     2-Cl        Et       Et            mp 71-72° C.                 66     2-Cl        Et                                                                                      ##STR98##    mp 105-106° C.               67     2-Cl        --CH.sub.2 CH═CH.sub.2                                                             Et                                                68     2-Cl        --CH.sub.2 C.tbd.CH                                                                    Et                                                69     2-Cl        --CH.sub.2 CH═CH.sub.2                                                              ##STR99##    mp 83-85° C.                 70     2-Cl        --CH.sub.2 C.tbd.CH                                                                     ##STR100##                                       71     2-Cl        i-Pr     i-Pr          mp 150-151° C.               72     2-Cl        i-Pr                                                                                    ##STR101##   n.sub.D.sup.18 1.5669               73     2-Cl        i-Pr                                                                                    ##STR102##   mp 125-127° C.               74     2-Cl        i-Pr                                                                                    ##STR103##   mp 131-133° C.               75     3-Cl        i-Pr                                                                                    ##STR104##   mp 154-155° C.               76     3-Cl        i-Pr                                                                                    ##STR105##   mp 173-174° C.               77     4-Cl        n-Pr                                                                                    ##STR106##                                       78     4-Cl        n-Bu                                                                                    ##STR107##                                       79     4-Cl        i-Bu                                                                                    ##STR108##                                       80     4-Cl        sec-Bu                                                                                  ##STR109##                                       81     4-Cl                                                                                       ##STR110##                                                                             ##STR111##                                       82     4-Cl        --CH.sub.2 CH═CH.sub.2                                                              ##STR112##                                       83     4-Cl        --CH.sub.2 C.tbd.CH                                                                     ##STR113##                                       84     4-Cl        i-Pr                                                                                    ##STR114##                                       85     4-Cl        i-Pr                                                                                    ##STR115##   mp 206-208° C.               86     4-Cl        i-Pr                                                                                    ##STR116##                                       87     4-Cl        i-Pr                                                                                    ##STR117##                                       88     4-Cl        i-Pr                                                                                    ##STR118##   mp 181-183° C.               89     4-Cl        i-Pr                                                                                    ##STR119##                                       90     4-Cl        i-Pr                                                                                    ##STR120##                                       91     4-Cl        i-Pr                                                                                    ##STR121##                                       92     4-Cl        i-Pr                                                                                    ##STR122##                                       93     4-Cl        i-Pr                                                                                    ##STR123##                                       94     4-Cl        i-Pr                                                                                    ##STR124##                                       95     4-Cl        i-Pr                                                                                    ##STR125##                                       96     4-Cl        i-Pr                                                                                    ##STR126##                                       97     4-Cl        i-Pr                                                                                    ##STR127##                                       98     4-Cl        i-Pr                                                                                    ##STR128##                                       99     4-Cl        i-Pr                                                                                    ##STR129##                                       100    4-Cl        i-Pr                                                                                    ##STR130##                                       101    4-Cl        i-Pr                                                                                    ##STR131##                                       102    4-Cl        i-Pr                                                                                    ##STR132##                                       103    4-Cl        i-Pr                                                                                    ##STR133##                                       104    4-Cl        i-Pr                                                                                    ##STR134##                                       105    4-Cl        i-Pr                                                                                    ##STR135##                                       106    4-Cl        i-Pr                                                                                    ##STR136##                                       107    4-Cl        i-Pr                                                                                    ##STR137##                                       108    4-Cl        i-Pr                                                                                    ##STR138##                                       109    4-Cl        i-Pr                                                                                    ##STR139##                                       110    4-Cl        i-Pr                                                                                    ##STR140##                                       111    4-Cl        i-Pr                                                                                    ##STR141##                                       112    4-Cl                                                                                       ##STR142##                                                                             ##STR143##                                       113    4-Cl                                                                                       ##STR144##                                                                             ##STR145##                                       114    4-Cl                                                                                       ##STR146##                                                                             ##STR147##                                       115    4-Cl        Et       Et                                                116    4-Cl        Et                                                                                      ##STR148##                                       117    4-Cl        --CH.sub.2 CH═CH.sub.2                                                             Et                                                118    4-Cl        --CH.sub.2 C.tbd.CH                                                                    Et                                                119    4-Cl        --CH.sub.2 CH═CH.sub.2                                                              ##STR149##                                       120    4-Cl        --CH.sub.2 C.tbd.CH                                                                     ##STR150##                                       121    4-Cl        i-Pr                                                                                    ##STR151##                                       122    4-Cl        i-Pr                                                                                    ##STR152##                                       123    4-Cl        i-Pr                                                                                    ##STR153##                                       124    4-Cl        i-Pr                                                                                    ##STR154##                                       125    2-Br        Me                                                                                      ##STR155##                                       126    2-Br        Et                                                                                      ##STR156##                                       127    2-Br        n-Pr                                                                                    ##STR157##                                       128    2-Br        n-Bu                                                                                    ##STR158##                                       129    2-Br        i-Bu                                                                                    ##STR159##                                       130    2-Br        sec-Bu                                                                                  ##STR160##                                       131    2-Br                                                                                       ##STR161##                                                                             ##STR162##                                       132    2-Br        --CH.sub.2 CH═CH.sub.2                                                              ##STR163##                                       133    2-Br        --CH.sub.2 C.tbd.CH                                                                     ##STR164##                                       134    2-Br        i-Pr                                                                                    ##STR165##                                       135    2-Br        i-Pr                                                                                    ##STR166##   mp 146-147° C.               136    2-Br        i-Pr                                                                                    ##STR167##                                       137    2-Br        i-Pr                                                                                    ##STR168##                                       138    2-Br        i-Pr                                                                                    ##STR169##   mp 104-105° C.               139    2-Br        i-Pr                                                                                    ##STR170##                                       140    2-Br        i-Pr                                                                                    ##STR171##                                       141    2-Br        i-Pr                                                                                    ##STR172##                                       142    2-Br        i-Pr                                                                                    ##STR173##                                       143    2-Br        i-Pr                                                                                    ##STR174##                                       144    2-Br        i-Pr                                                                                    ##STR175##                                       145    2-Br        i-Pr                                                                                    ##STR176##                                       146    2-Br        i-Pr                                                                                    ##STR177##                                       147    2-Br        i-Pr                                                                                    ##STR178##                                       148    2-Br        i-Pr                                                                                    ##STR179##                                       149    2-Br        i-Pr                                                                                    ##STR180##                                       150    2-Br        i-Pr                                                                                    ##STR181##                                       151    2-Br        i-Pr                                                                                    ##STR182##                                       152    2-Br        i-Pr                                                                                    ##STR183##                                       153    2-Br        i-Pr                                                                                    ##STR184##                                       154    2-Br        i-Pr                                                                                    ##STR185##                                       155    2-Br        i-Pr                                                                                    ##STR186##                                       156    2-Br        i-Pr                                                                                    ##STR187##                                       157    2-Br        i-Pr                                                                                    ##STR188##                                       158    2-Br        i-Pr                                                                                    ##STR189##                                       159    2-Br        i-Pr                                                                                    ##STR190##                                       160    2-Br        i-Pr                                                                                    ##STR191##                                       161    2-Br        i-Pr                                                                                    ##STR192##                                       162    2-Br                                                                                       ##STR193##                                                                             ##STR194##                                       163    2-Br                                                                                       ##STR195##                                                                             ##STR196##                                       164    2-F                                                                                        ##STR197##                                                                            Et            n.sub.D.sup.18 1.5414               165    2-F         i-Pr                                                                                    ##STR198##   mp 126-127° C.               166    2-F         i-Pr                                                                                    ##STR199##   mp 135-136° C.               167    3-F         i-Pr                                                                                    ##STR200##   mp 134-136° C.               168    3-F         i-Pr                                                                                    ##STR201##   mp 140-141° C.               169    4-F         i-Pr                                                                                    ##STR202##   mp 120-121° C.               170    4-F         i-Pr                                                                                    ##STR203##   mp 151-152° C.               171    2,4-F.sub.2 Me                                                                                      ##STR204##                                       172    2,4-F.sub.2 Et                                                                                      ##STR205##                                       173    2,4-F.sub.2 n-Pr                                                                                    ##STR206##                                       174    2,4-F.sub.2 n-Bu                                                                                    ##STR207##                                       175    2,4-F.sub.2 i-Bu                                                                                    ##STR208##                                       176    2,4-F.sub.2 sec-Bu                                                                                  ##STR209##                                       177    2,4-F.sub.2                                                                                ##STR210##                                                                             ##STR211##                                       178    2,4-F.sub.2 --CH.sub.2 CH═CH.sub.2                                                              ##STR212##                                       179    2,4-F.sub.2 --CH.sub.2 C.tbd.CH                                                                     ##STR213##                                       180    2,4-F.sub.2 i-Pr                                                                                    ##STR214##                                       181    2,4-F.sub.2 i-Pr                                                                                    ##STR215##   mp 166-167° C.               182    2,4-F.sub.2 i-Pr                                                                                    ##STR216##                                       183    2,4-F.sub.2 i-Pr                                                                                    ##STR217##                                       184    2,4-F.sub.2 i-Pr                                                                                    ##STR218##   mp 142-143° C.               185    2,4-F.sub.2 i-Pr                                                                                    ##STR219##                                       186    2,4-F.sub.2 i-Pr                                                                                    ##STR220##                                       187    2,4-F.sub.2 i-Pr                                                                                    ##STR221##                                       188    2,4-F.sub.2 i-Pr                                                                                    ##STR222##                                       189    2,4-F.sub.2 i-Pr                                                                                    ##STR223##                                       190    2,4-F.sub.2 i-Pr                                                                                    ##STR224##                                       191    2,4-F.sub.2 i-Pr                                                                                    ##STR225##                                       192    2,4-F.sub.2 i-Pr                                                                                    ##STR226##                                       193    2,4-F.sub.2 i-Pr                                                                                    ##STR227##                                       194    2,4-F.sub.2 i-Pr                                                                                    ##STR228##                                       195    2,4-F.sub.2 i-Pr                                                                                    ##STR229##                                       196    2,4-F.sub.2 i-Pr                                                                                    ##STR230##                                       197    2,4-F.sub.2 i-Pr                                                                                    ##STR231##                                       198    2,4-F.sub.2 i-Pr                                                                                    ##STR232##                                       199    2,5-F.sub.2 i-Pr                                                                                    ##STR233##   mp 105-107° C.               200    2,5-F.sub.2 i-Pr                                                                                    ##STR234##   mp 126-127° C.               201    2,4-F.sub.2 i-Pr                                                                                    ##STR235##                                       202    2,4-F.sub.2 i-Pr                                                                                    ##STR236##                                       203    2,4-F.sub.2 i-Pr                                                                                    ##STR237##                                       204    2,4-F.sub.2 i-Pr                                                                                    ##STR238##                                       205    2,4-F.sub.2 i-Pr                                                                                    ##STR239##                                       206    2,4-F.sub.2 i-Pr                                                                                    ##STR240##                                       207    2,4-F.sub.2 i-Pr                                                                                    ##STR241##                                       208    2,4-F.sub.2                                                                                ##STR242##                                                                             ##STR243##                                       209    2,4-F.sub.2                                                                                ##STR244##                                                                             ##STR245##                                       210    2,4-F.sub.2                                                                                ##STR246##                                                                             ##STR247##                                       211    2,4-F.sub.2 Et       Et                                                212    2,4-F.sub.2 Et                                                                                      ##STR248##                                       213    2,4-F.sub.2 --CH.sub.2 CH═CH.sub.2                                                             Et                                                214    2,4-F.sub.2 --CH.sub.2 C.tbd.CH                                                                    Et                                                215    2,4-F.sub.2 --CH.sub.2 CH═CH.sub.2                                                              ##STR249##                                       216    2,4-F.sub.2 --CH.sub.2 C.tbd.CH                                                                     ##STR250##                                       217    2,4-F.sub.2 i-Pr                                                                                    ##STR251##                                       218    2,4-F.sub.2 i-Pr                                                                                    ##STR252##                                       219    2,4-F.sub.2 i-Pr                                                                                    ##STR253##                                       220    2,4-F.sub.2 i-Pr                                                                                    ##STR254##                                       221    2,3-Cl.sub.2                                                                              i-Pr                                                                                    ##STR255##   mp 107-108° C.               222    2,3-Cl.sub.2                                                                              i-Pr                                                                                    ##STR256##   mp 103-104° C.               223    2,4-Cl.sub.2                                                                              n-Pr                                                                                    ##STR257##                                       224    2,4-Cl.sub.2                                                                              n-Bu                                                                                    ##STR258##                                       225    2,4-Cl.sub.2                                                                              i-Bu                                                                                    ##STR259##                                       226    2,4-Cl.sub.2                                                                              sec-Bu                                                                                  ##STR260##                                       227    2,4-Cl.sub.2                                                                               ##STR261##                                                                             ##STR262##                                       228    2,4-Cl.sub.2                                                                              --CH.sub.2 CH═CH.sub.2                                                              ##STR263##                                       229    2,4-Cl.sub.2                                                                              --CH.sub.2 C.tbd.CH                                                                     ##STR264##                                       230    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR265##                                       231    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR266##   mp 129-131° C.               232    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR267##                                       233    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR268##                                       234    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR269##   mp 170-172° C.               235    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR270##                                       236    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR271##                                       237    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR272##                                       238    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR273##                                       239    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR274##                                       240    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR275##                                       241    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR276##                                       242    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR277##                                       243    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR278##                                       244    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR279##                                       245    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR280##                                       246    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR281##                                       247    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR282##                                       248    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR283##                                       249    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR284##                                       250    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR285##                                       251    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR286##                                       252    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR287##                                       253    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR288##                                       254    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR289##                                       255    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR290##                                       256    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR291##                                       257    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR292##                                       258    2,4-Cl.sub.2                                                                               ##STR293##                                                                             ##STR294##                                       259    2,4-Cl.sub.2                                                                               ##STR295##                                                                             ##STR296##                                       260    2,4-Cl.sub.2                                                                               ##STR297##                                                                             ##STR298##                                       261    2,4-Cl.sub.2                                                                              Et       Et                                                262    2,4-Cl.sub.2                                                                              Et                                                                                      ##STR299##                                       263    2,4-Cl.sub.2                                                                              --CH.sub.2 CH═CH.sub.2                                                             Et                                                264    2,4-Cl.sub.2                                                                              --CH.sub.2 C.tbd.CH                                                                    Et                                                265    2,4-Cl.sub.2                                                                              --CH.sub.2 CH═CH.sub.2                                                              ##STR300##                                       266    2,4-Cl.sub.2                                                                              --CH.sub.2 C.tbd.CH                                                                     ##STR301##                                       267    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR302##                                       268    2,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR303##                                       269    2,5-Cl.sub.2                                                                              i-Pr                                                                                    ##STR304##   mp 163-164° C.               270    2,5-Cl.sub.2                                                                              i-Pr                                                                                    ##STR305##   mp 149-150° C.               271    2,6-Cl.sub.2                                                                              Me                                                                                      ##STR306##                                       272    2,6-Cl.sub.2                                                                              Et                                                                                      ##STR307##                                       273    2,6-Cl.sub.2                                                                              n-Pr                                                                                    ##STR308##                                       274    2,6-Cl.sub.2                                                                              n-Bu                                                                                    ##STR309##                                       275    2,6-Cl.sub.2                                                                              i-Bu                                                                                    ##STR310##                                       276    2,6-Cl.sub.2                                                                              sec-Bu                                                                                  ##STR311##                                       277    2,6-Cl.sub.2                                                                               ##STR312##                                                                             ##STR313##                                       278    2,6-Cl.sub.2                                                                              --CH.sub.2 CH═CH.sub.2                                                              ##STR314##                                       279    2,6-Cl.sub.2                                                                              --CH.sub.2 C.tbd.CH                                                                     ##STR315##                                       280    2.6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR316##                                       281    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR317##   mp 129-131° C.               282    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR318##                                       283    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR319##                                       284    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR320##   mp 223-225° C.               285    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR321##                                       286    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR322##                                       287    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR323##                                       288    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR324##                                       289    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR325##                                       290    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR326##                                       291    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR327##                                       292    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR328##                                       293    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR329##                                       294    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR330##                                       295    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR331##                                       296    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR332##                                       297    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR333##                                       298    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR334##                                       299    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR335##                                       300    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR336##                                       301    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR337##                                       302    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR338##                                       303    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR339##                                       304    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR340##                                       305    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR341##                                       306    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR342##                                       307    2,6-Cl.sub.2                                                                              i-Pr                                                                                    ##STR343##                                       308    2,6-Cl.sub.2                                                                               ##STR344##                                                                             ##STR345##                                       309    2,6-Cl.sub.2                                                                               ##STR346##                                                                             ##STR347##                                       310    2,6-Cl.sub.2                                                                               ##STR348##                                                                             ##STR349##                                       311    2,6-Cl.sub.2                                                                              Et       Et                                                312    2,6-Cl.sub.2                                                                              Et                                                                                      ##STR350##                                       313    2,6-Cl.sub.2                                                                              --CH.sub.2 CH═CH.sub.2                                                             Et                                                314    2,6-Cl.sub.2                                                                              --CH.sub.2 C.tbd.CH                                                                    Et                                                315    2,6-Cl.sub.2                                                                              --CH.sub.2 CH═CH.sub.2                                                              ##STR351##                                       316    2,6-Cl.sub.2                                                                              --CH.sub.2 C.tbd.CH                                                                     ##STR352##                                       317    3,5-Cl.sub.2                                                                              i-Pr                                                                                    ##STR353##   mp 179-181° C.               318    3,5-Cl.sub.2                                                                              i-Pr                                                                                    ##STR354##   mp 124-126° C.               319    3,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR355##   mp 146-147° C.               320    3,4-Cl.sub.2                                                                              i-Pr                                                                                    ##STR356##   mp 176-177° C.               321    2-F, 4-Cl   i-Pr                                                                                    ##STR357##   mp 171-172° C.               322    2-F, 4-Cl   i-Pr                                                                                    ##STR358##   mp 199-200° C.               323    2-Cl, 4-F   i-Pr                                                                                    ##STR359##   mp 121-122° C.               324    2-Cl, 4-F   i-Pr                                                                                    ##STR360##   mp 122-124° C.               325    2-Me        i-Bu                                                                                    ##STR361##                                       326    2-Me        sec-Bu                                                                                  ##STR362##                                       327    2-Me                                                                                       ##STR363##                                                                             ##STR364##                                       328    2-Me        --CH.sub.2 CH═CH.sub.2                                                              ##STR365##                                       329    2-Me        --CH.sub.2 C.tbd.CH                                                                     ##STR366##                                       330    2-Me        i-Pr                                                                                    ##STR367##                                       331    2-Me        i-Pr                                                                                    ##STR368##   mp 106-107° C.               332    2-Me        i-Pr                                                                                    ##STR369##   mp 96-98° C.                 333    2-Me        i-Pr                                                                                    ##STR370##                                       334    2-Me        i-Pr                                                                                    ##STR371##   mp 94-95° C.                 335    2-Me        i-Pr                                                                                    ##STR372##                                       336    2-Me        i-Pr                                                                                    ##STR373##                                       337    2-Me        i-Pr                                                                                    ##STR374##                                       338    2-Me        i-Pr                                                                                    ##STR375##                                       339    2-Me        i-Pr                                                                                    ##STR376##                                       340    2-Me        i-Pr                                                                                    ##STR377##                                       341    2-Me        i-Pr                                                                                    ##STR378##                                       342    2-Me        i-Pr                                                                                    ##STR379##                                       343    2-Me        i-Pr                                                                                    ##STR380##                                       344    2-Me        i-Pr                                                                                    ##STR381##                                       345    2-Me        i-Pr                                                                                    ##STR382##                                       346    2-Me        i-Pr                                                                                    ##STR383##                                       347    2-Me        i-Pr                                                                                    ##STR384##                                       348    2-Me        i-Pr                                                                                    ##STR385##                                       349    2-Me        i-Pr                                                                                    ##STR386##                                       350    2-Me        i-Pr                                                                                    ##STR387##                                       351    2-Me        i-Pr                                                                                    ##STR388##                                       352    2-Me        i-Pr                                                                                    ##STR389##                                       353    2-Me        i-Pr                                                                                    ##STR390##                                       354    2-Me        i-Pr                                                                                    ##STR391##                                       355    2-Me        i-Pr                                                                                    ##STR392##                                       356    2-Me        i-Pr                                                                                    ##STR393##                                       357    2-Me        i-Pr                                                                                    ##STR394##                                       358    2-Me                                                                                       ##STR395##                                                                             ##STR396##                                       359    2-Me                                                                                       ##STR397##                                                                             ##STR398##                                       360    2-Me        n-Pr                                                                                    ##STR399##   n.sub.D.sup.18 1.5511               361    2-Me        Et       Et                                                362    2-Me        i-Pr                                                                                    ##STR400##   mp 116-117° C.               363    2-Me        --CH.sub.2 CH═CH.sub.2                                                             Et                                                364    2-Me        --CH.sub.2 C.tbd.CH                                                                    Et                                                365    2-Me        --CH.sub.2 CH═CH.sub.2                                                              ##STR401##   mp 72-74° C.                 366    2-Me        --CH.sub.2 C.tbd.CH                                                                     ##STR402##                                       367    2-Me        i-Pr                                                                                    ##STR403##                                       368    2-Me        i-Pr                                                                                    ##STR404##                                       369    2-Me        i-Pr                                                                                    ##STR405##                                       370    2-Me        i-Pr                                                                                    ##STR406##                                       371    3-Me        Me                                                                                      ##STR407##                                       372    3-Me        Et                                                                                      ##STR408##                                       373    3-Me        n-Pr                                                                                    ##STR409##                                       374    3-Me        n-Bu                                                                                    ##STR410##                                       375    3-Me        i-Bu                                                                                    ##STR411##                                       376    3-Me        sec-Bu                                                                                  ##STR412##                                       377    3-Me                                                                                       ##STR413##                                                                             ##STR414##                                       378    3-Me        --CH.sub.2 CH═CH.sub.2                                                              ##STR415##                                       379    3-Me        --CH.sub.2 C.tbd.CH                                                                     ##STR416##                                       380    3-Me        i-Pr                                                                                    ##STR417##                                       381    3-Me        i-Pr                                                                                    ##STR418##   mp 133-134° C.               382    3-Me        i-Pr                                                                                    ##STR419##                                       383    3-Me        i-Pr                                                                                    ##STR420##                                       384    3-Me        i-Pr                                                                                    ##STR421##   mp 150-151° C.               385    3-Me        i-Pr                                                                                    ##STR422##                                       386    3-Me        i-Pr                                                                                    ##STR423##                                       387    3-Me        i-Pr                                                                                    ##STR424##                                       388    3-Me        i-Pr                                                                                    ##STR425##                                       389    3-Me        i-Pr                                                                                    ##STR426##                                       390    3-Me        i-Pr                                                                                    ##STR427##                                       391    3-Me        i-Pr                                                                                    ##STR428##                                       392    3-Me        i-Pr                                                                                    ##STR429##                                       393    3-Me        i-Pr                                                                                    ##STR430##                                       394    3-Me        i-Pr                                                                                    ##STR431##                                       395    3-Me        i-Pr                                                                                    ##STR432##                                       396    3-Me        i-Pr                                                                                    ##STR433##                                       397    3-Me        i-Pr                                                                                    ##STR434##                                       398    3-Me        i-Pr                                                                                    ##STR435##                                       399    3-Me        i-Pr                                                                                    ##STR436##                                       400    3-Me        i-Pr                                                                                    ##STR437##                                       401    3-Me        i-Pr                                                                                    ##STR438##                                       402    3-Me        i-Pr                                                                                    ##STR439##                                       403    3-Me        i-Pr                                                                                    ##STR440##                                       404    3-Me        i-Pr                                                                                    ##STR441##                                       405    3-Me        i-Pr                                                                                    ##STR442##                                       406    3-Me        i-Pr                                                                                    ##STR443##                                       407    3-Me        i-Pr                                                                                    ##STR444##                                       408    3-Me                                                                                       ##STR445##                                                                             ##STR446##                                       409    3-Me                                                                                       ##STR447##                                                                             ##STR448##                                       410    3-Me                                                                                       ##STR449##                                                                             ##STR450##                                       411    3-Me        Et       Et                                                412    3-Me        Et                                                                                      ##STR451##                                       413    3-Me        --CH.sub.2 CH═CH.sub.2                                                             Et                                                414    3-Me        --CH.sub.2 C.tbd.CH                                                                    Et                                                415    3-Me        --CH.sub.2 CH═CH.sub.2                                                              ##STR452##                                       416    3-Me        --CH.sub.2 C.tbd.CH                                                                     ##STR453##                                       417    3-Me        i-Pr                                                                                    ##STR454##                                       418    3-Me        i-Pr                                                                                    ##STR455##                                       419    3-Me        i-Pr                                                                                    ##STR456##                                       420    3-Me        i-Pr                                                                                    ##STR457##                                       421    4-Me        Me                                                                                      ##STR458##                                       422    4-Me        Et                                                                                      ##STR459##                                       423    4-Me        n-Pr                                                                                    ##STR460##                                       424    4-Me        n-Bu                                                                                    ##STR461##                                       425    4-Me        i-Bu                                                                                    ##STR462##                                       426    4-Me        sec-Bu                                                                                  ##STR463##                                       427    4-Me                                                                                       ##STR464##                                                                             ##STR465##                                       428    4-Me        --CH.sub.2 CH═CH.sub.2                                                              ##STR466##                                       429    4-Me        --CH.sub.2 C.tbd.CH                                                                     ##STR467##                                       430    4-Me        i-Pr                                                                                    ##STR468##                                       431    4-Me        i-Pr                                                                                    ##STR469##   mp 164-165° C.               432    4-Me        i-Pr                                                                                    ##STR470##                                       433    4-Me        i-Pr                                                                                    ##STR471##                                       434    4-Me        i-Pr                                                                                    ##STR472##   mp 153-155° C.               435    4-Me        i-Pr                                                                                    ##STR473##                                       436    4-Me        i-Pr                                                                                    ##STR474##                                       437    4-Me        i-Pr                                                                                    ##STR475##                                       438    4-Me        i-Pr                                                                                    ##STR476##                                       439    4-Me        i-Pr                                                                                    ##STR477##                                       440    4-Me        i-Pr                                                                                    ##STR478##                                       441    4-Me        i-Pr                                                                                    ##STR479##                                       442    4-Me        i-Pr                                                                                    ##STR480##                                       443    4-Me        i-Pr                                                                                    ##STR481##                                       444    4-Me        i-Pr                                                                                    ##STR482##                                       445    4-Me        i-Pr                                                                                    ##STR483##                                       446    4-Me        i-Pr                                                                                    ##STR484##                                       447    4-Me        i-Pr                                                                                    ##STR485##                                       448    4-Me        i-Pr                                                                                    ##STR486##                                       449    4-Me        i-Pr                                                                                    ##STR487##                                       450    4-Me        i-Pr                                                                                    ##STR488##                                       451    4-Me        i-Pr                                                                                    ##STR489##                                       452    4-Me        i-Pr                                                                                    ##STR490##                                       453    4-Me        i-Pr                                                                                    ##STR491##                                       454    4-Me        i-Pr                                                                                    ##STR492##                                       455    4-Me        i-Pr                                                                                    ##STR493##                                       456    4-Me        i-Pr                                                                                    ##STR494##                                       457    4-Me        i-Pr                                                                                    ##STR495##                                       458    4-Me                                                                                       ##STR496##                                                                             ##STR497##                                       459    4-Me                                                                                       ##STR498##                                                                             ##STR499##                                       460    4-Me                                                                                       ##STR500##                                                                             ##STR501##                                       461    4-Me        Et       Et                                                462    4-Me        Et                                                                                      ##STR502##                                       463    4-Me        --CH.sub.2 CH═CH.sub.2                                                             Et                                                464    4-Me        --CH.sub.2 C.tbd.CH                                                                    Et                                                465    4-Me        --CH.sub.2 CH═CH.sub.2                                                              ##STR503##                                       466    4-Me        --CH.sub.2 C.tbd.CH                                                                     ##STR504##                                       467    4-Me        i-Pr                                                                                    ##STR505##                                       468    4-Me        i-Pr                                                                                    ##STR506##                                       469    4-Me        i-Pr                                                                                    ##STR507##                                       470    4-Me        i-Pr                                                                                    ##STR508##                                       471    2-Et        Me                                                                                      ##STR509##                                       472    2-Et        Et                                                                                      ##STR510##                                       473    2-Et        n-Pr                                                                                    ##STR511##                                       474    2-Et        n-Bu                                                                                    ##STR512##                                       475    2-Et        i-Bu                                                                                    ##STR513##                                       476    2-Et        sec-Bu                                                                                  ##STR514##                                       477    2-Et                                                                                       ##STR515##                                                                             ##STR516##                                       478    2-Et        --CH.sub.2 CH═CH.sub.2                                                              ##STR517##                                       479    2-Et        --CH.sub.2 C.tbd.CH                                                                     ##STR518##                                       480    2-Et        i-Pr                                                                                    ##STR519##                                       481    2-Et        i-Pr                                                                                    ##STR520##   mp 66-68° C.                 482    2-Et        i-Pr                                                                                    ##STR521##                                       483    2-Et        i-Pr                                                                                    ##STR522##                                       484    2-Et        i-Pr                                                                                    ##STR523##   n.sub.D.sup.18 1.5483               485    2-Et        i-Pr                                                                                    ##STR524##                                       486    2-Et        i-Pr                                                                                    ##STR525##                                       487    2-Et        i-Pr                                                                                    ##STR526##                                       488    2-Et        i-Pr                                                                                    ##STR527##                                       489    2-Et        i-Pr                                                                                    ##STR528##                                       490    2-Et        i-Pr                                                                                    ##STR529##                                       491    2-Et        i-Pr                                                                                    ##STR530##                                       492    2-Et        i-Pr                                                                                    ##STR531##                                       493    2-Et        i-Pr                                                                                    ##STR532##                                       494    2-Et        i-Pr                                                                                    ##STR533##                                       495    2-Et        i-Pr                                                                                    ##STR534##                                       496    2-Et        i-Pr                                                                                    ##STR535##                                       497    2-Et        i-Pr                                                                                    ##STR536##                                       498    2-Et        i-Pr                                                                                    ##STR537##                                       499    2-Et        i-Pr                                                                                    ##STR538##                                       500    2-Et        i-Pr                                                                                    ##STR539##                                       501    2-Et        i-Pr                                                                                    ##STR540##                                       502    2-Et        i-Pr                                                                                    ##STR541##                                       503    2-Et        i-Pr                                                                                    ##STR542##                                       504    2-Et        i-Pr                                                                                    ##STR543##                                       505    2-Et        i-Pr                                                                                    ##STR544##                                       506    2-Et        i-Pr                                                                                    ##STR545##                                       507    2-Et        i-Pr                                                                                    ##STR546##                                       508    2-Et                                                                                       ##STR547##                                                                             ##STR548##                                       509    2-Et                                                                                       ##STR549##                                                                             ##STR550##                                       510    2-Et                                                                                       ##STR551##                                                                             ##STR552##                                       511    2-Et        Et       Et                                                512    2-Et        Et                                                                                      ##STR553##                                       513    2-Et        --CH.sub.2 CH═CH.sub.2                                                             Et                                                514    2-Et        --CH.sub.2 C.tbd.CH                                                                    Et                                                515    2-Et        --CH.sub.2 CH═CH.sub.2                                                              ##STR554##                                       516    2-Et        --CH.sub.2 C.tbd.CH                                                                     ##STR555##                                       517    2-n-Pr      i-Pr                                                                                    ##STR556##   mp 100-101° C.               518    2-n-Pr      i-Pr                                                                                    ##STR557##   mp 57-59° C.                 519    2-i-Pr      i-Pr                                                                                    ##STR558##   mp 139-140° C.               520    2-i-Pr      i-Pr                                                                                    ##STR559##   mp 92-93° C.                 521    2-MeO       i-Pr                                                                                    ##STR560##   mp 107-109° C.               522    2-MeO       i-Pr                                                                                    ##STR561##   mp 113-115° C.               523    3-MeO       i-Pr                                                                                    ##STR562##                                       524    3-MeO       i-Pr                                                                                    ##STR563##   mp 150-151° C.               525    4-MeO       i-Bu                                                                                    ##STR564##                                       526    4-MeO       sec-Bu                                                                                  ##STR565##                                       527    4-MeO                                                                                      ##STR566##                                                                             ##STR567##                                       528    4-MeO       --CH.sub.2 CH═CH.sub.2                                                              ##STR568##                                       529    4-MeO       --CH.sub.2 C.tbd.CH                                                                     ##STR569##                                       530    4-MeO       i-Pr                                                                                    ##STR570##                                       531    4-MeO       i-Pr                                                                                    ##STR571##   mp 148-149° C.               532    4-MeO       i-Pr                                                                                    ##STR572##                                       533    4-MeO       i-Pr                                                                                    ##STR573##                                       534    4-MeO       i-Pr                                                                                    ##STR574##   mp 125-126° C.               535    4-MeO       i-Pr                                                                                    ##STR575##                                       536    4-MeO       i-Pr                                                                                    ##STR576##                                       537    4-MeO       i-Pr                                                                                    ##STR577##                                       538    4-MeO       i-Pr                                                                                    ##STR578##                                       539    4-MeO       i-Pr                                                                                    ##STR579##                                       540    4-MeO       i-Pr                                                                                    ##STR580##                                       541    4-MeO       i-Pr                                                                                    ##STR581##                                       542    4-MeO       i-Pr                                                                                    ##STR582##                                       543    4-MeO       i-Pr                                                                                    ##STR583##                                       544    4-MeO       i-Pr                                                                                    ##STR584##                                       545    4-MeO       i-Pr                                                                                    ##STR585##                                       546    4-MeO       i-Pr                                                                                    ##STR586##                                       547    4-MeO       i-Pr                                                                                    ##STR587##                                       548    4-MeO       i-Pr                                                                                    ##STR588##                                       549    4-MeO       i-Pr                                                                                    ##STR589##                                       550    4-MeO       i-Pr                                                                                    ##STR590##                                       551    4-MeO       i-Pr                                                                                    ##STR591##                                       552    4-MeO       i-Pr                                                                                    ##STR592##                                       553    4-MeO       i-Pr                                                                                    ##STR593##                                       554    4-MeO       i-Pr                                                                                    ##STR594##                                       555    4-MeO       i-Pr                                                                                    ##STR595##                                       556    4-MeO       i-Pr                                                                                    ##STR596##                                       557    4-MeO       i-Pr                                                                                    ##STR597##                                       558    4-MeO                                                                                      ##STR598##                                                                             ##STR599##                                       559    4-MeO                                                                                      ##STR600##                                                                             ##STR601##                                       560    4-MeO                                                                                      ##STR602##                                                                             ##STR603##                                       561    4-MeO       Et       Et                                                562    4-MeO       Et                                                                                      ##STR604##                                       563    4-MeO       --CH.sub.2 CH═CH.sub.2                                                             Et                                                564    4-MeO       --CH.sub.2 C.tbd.CH                                                                    Et                                                565    4-MeO       --CH.sub.2 CH═CH.sub.2                                                              ##STR605##                                       566    4-MeO       --CH.sub.2 C.tbd.CH                                                                     ##STR606##                                       567    4-MeO       i-Pr                                                                                    ##STR607##                                       568    4-MeO       i-Pr                                                                                    ##STR608##                                       569    3,5-(MeO).sub.2                                                                           i-Pr                                                                                    ##STR609##                                       570    3,5-(MeO).sub.2                                                                           i-Pr                                                                                    ##STR610##   mp 99-100° C.                571    2-Cl, 6-Me  i-Pr                                                                                    ##STR611##   mp 204-205° C.               572    2-Cl, 6-Me  i-Pr                                                                                    ##STR612##   mp 94-96° C.                 573    2-Cl, 6-Me  i-Pr                                                                                    ##STR613##                                       574    2-Cl, 6-Me  Et                                                                                      ##STR614##                                       575    2-Cl, 6-Me  Et       Et                                                576    2,6-(Me).sub.2                                                                            i-Pr                                                                                    ##STR615##   mp 190-191° C.               577    2,6-(Me).sub.2                                                                            i-Pr                                                                                    ##STR616##   mp 101-102° C.               578    2,6-(Me).sub.2                                                                            i-Pr                                                                                    ##STR617##                                       579    2,6-(Me).sub.2                                                                            Et                                                                                      ##STR618##                                       580    2,6-(Me).sub.2                                                                            Et       Et                                                581    2,4-(Me).sub.2                                                                            i-Pr                                                                                    ##STR619##   mp 133-134° C.               582    2,4-(Me).sub.2                                                                            i-Pr                                                                                    ##STR620##   mp 91-93° C.                 583    2,4-(Me).sub.2                                                                            i-Pr                                                                                    ##STR621##                                       584    2,4-(Me).sub.2                                                                            Et                                                                                      ##STR622##                                       585    2,4-(Me).sub.2                                                                            Et       Et                                                586    2,5-(Me).sub.2                                                                            i-Pr                                                                                    ##STR623##   mp 125-127° C.               587    2,5-(Me).sub.2                                                                            i-Pr                                                                                    ##STR624##   mp 86-88° C.                 588    2,5-(Me).sub.2                                                                            i-Pr                                                                                    ##STR625##                                       589    2,5-(Me).sub.2                                                                            Et                                                                                      ##STR626##                                       590    2,5-(Me).sub.2                                                                            Et       Et                                                591    2,3-(Me).sub.2                                                                            i-Pr                                                                                    ##STR627##   mp 122-124° C.               592    2,3-(Me).sub.2                                                                            i-Pr                                                                                    ##STR628##   mp 109-110° C.               593    2,3-(Me).sub.2                                                                            i-Pr                                                                                    ##STR629##                                       594    2-Et, 6-Me  i-Pr                                                                                    ##STR630##   mp 115-117° C.               595    2-Et, 6-Me  i-Pr                                                                                    ##STR631##   mp 97-99° C.                 596    2-CF.sub.3  i-Pr                                                                                    ##STR632##   mp 129-130° C.               597    2-CF.sub.3  i-Pr                                                                                    ##STR633##   mp 106-107° C.               598    2-CF.sub.3  i-Pr                                                                                    ##STR634##                                       599    3-CF.sub.3  i-Pr                                                                                    ##STR635##   mp 171-172° C.               600    3-CF.sub.3  i-Pr                                                                                    ##STR636##   mp 188-189° C.               601    4-CF.sub.3  i-Pr                                                                                    ##STR637##   mp 161-162° C.               602    4-CF.sub.3  i-Pr                                                                                    ##STR638##   mp 192-193° C.               603    4-CF.sub.3  i-Pr                                                                                    ##STR639##                                       604    4-CF.sub.3  Et                                                                                      ##STR640##                                       605    4-CF.sub.3  Et       Et                                                606    2-CHF.sub.2 O                                                                             i-Pr                                                                                    ##STR641##                                       607    2-CHF.sub.2 O                                                                             i-Pr                                                                                    ##STR642##                                       608    2-CHF.sub.2 O                                                                             i-Pr                                                                                    ##STR643##                                       609    2-CHF.sub.2 O                                                                             Et                                                                                      ##STR644##                                       610    2-CHF.sub.2 O                                                                             Et       Et                                                611    2-CF.sub.3 O                                                                              i-Pr                                                                                    ##STR645##   mp 91-92° C.                 612    2-CF.sub.3 O                                                                              i-Pr                                                                                    ##STR646##   mp 80-82° C.                 613    2-CF.sub.3 O                                                                              i-Pr                                                                                    ##STR647##                                       614    2-CF.sub.3 O                                                                              Et                                                                                      ##STR648##                                       615    2-CF.sub.3 O                                                                              Et       Et                                                616    2,4,6-(Me).sub.3                                                                          i-Pr                                                                                    ##STR649##                                       617    2,4,6-(Me).sub.3                                                                          i-Pr                                                                                    ##STR650##   mp 141-143° C.               618    2,4,6-(Me).sub.3                                                                          i-Pr                                                                                    ##STR651##                                       619    2,4,6-(Me).sub.3                                                                          Et                                                                                      ##STR652##                                       620    2,4,6-(Me).sub.3                                                                          Et       Et                                                621    2,4,6-Cl.sub.3                                                                            i-Pr                                                                                    ##STR653##   mp 183-185° C.               622    2,4,6-Cl.sub.3                                                                            i-Pr                                                                                    ##STR654##                                       623                                                                                   ##STR655## i-Pr                                                                                    ##STR656##   mp 121-122° C.               624                                                                                   ##STR657## i-Pr                                                                                    ##STR658##   mp 132-133° C.               625    2-MeS       i-Pr                                                                                    ##STR659##   mp 112-114° C.               626    2-MeS       i-Pr                                                                                    ##STR660##   mp 98-100° C.                627    2-MeSO      i-Pr                                                                                    ##STR661##   mp 111-112° C.               628    2-MeSO      i-Pr                                                                                    ##STR662##                                       629    2-MeSO.sub.2                                                                              i-Pr                                                                                    ##STR663##   mp 176-177° C.               630    2-MeSO.sub.2                                                                              i-Pr                                                                                    ##STR664##                                       631    2-CF.sub.3, 4-Cl                                                                          i-Pr                                                                                    ##STR665##   mp 124-125° C.               632    2-CF.sub.3, 4-Cl                                                                          i-Pr                                                                                    ##STR666##   mp 154-155° C.               633    2-Cl, 4-Me  i-Pr                                                                                    ##STR667##   mp 139-140° C.               634    2-Cl, 4-Me  i-Pr                                                                                    ##STR668##   mp 178-179° C.               635    2-Me, 4-Cl  i-Pr                                                                                    ##STR669##   mp 136-137° C.               636    2-Me, 4-Cl  i-Pr                                                                                    ##STR670##   mp 142-143° C.               637    2-Me, 3-Cl  i-Pr                                                                                    ##STR671##   mp 111-112° C.               638    2-Me, 3-Cl  i-Pr                                                                                    ##STR672##   mp 121-122° C.               639    2-Me, 5-Cl  i-Pr                                                                                    ##STR673##   mp 136-137° C.               640    2-Me, 5-Cl  i-Pr                                                                                    ##STR674##   mp 146-147° C.               641    2-CN        i-Pr                                                                                    ##STR675##   mp 115-117° C.               642    2-CN        i-Pr                                                                                    ##STR676##   mp 126-127° C.               643    2-NO.sub.2  i-Pr                                                                                    ##STR677##   mp 131-132° C.               644    2-NO.sub.2  i-Pr                                                                                    ##STR678##   mp 135-136° C.               645    2-NHCOMe    i-Pr                                                                                    ##STR679##   mp 105-107° C.               646    2-NHCOMe    i-Pr                                                                                    ##STR680##   n.sub.D.sup.18 1.5576               647    2-NHCOCF.sub.3                                                                            i-Pr                                                                                    ##STR681##   mp 132-133° C.               648    2-NHCOCF.sub.3                                                                            i-Pr                                                                                    ##STR682##   mp 143-144° C.               __________________________________________________________________________

                                      TABLE 1b                                    __________________________________________________________________________    General formula (Ib):                                                          ##STR683##                                                                   where A.sup.a means 1-naphthyl group                                           ##STR684##                                                                   or 5,6,7,8-tetrahydro-1-naphthyl group                                         ##STR685##                                                                   Compound No.                                                                         A.sup.a --                                                                             R.sub.1                                                                          R.sub.2    Physical data                                   __________________________________________________________________________    649                                                                                   ##STR686##                                                                            i-Pr                                                                              ##STR687##                                                                              mp 90-92° C.                             650                                                                                   ##STR688##                                                                            i-Pr                                                                              ##STR689##                                                                              mp 95-96° C.                             651                                                                                   ##STR690##                                                                            i-Pr                                                                              ##STR691##                                                                              mp 130-131° C.                           652                                                                                   ##STR692##                                                                            i-Pr                                                                              ##STR693##                                                                              mp 77-78° C.                             __________________________________________________________________________

                                      TABLE 1c                                    __________________________________________________________________________    General formula (Ic):                                                          ##STR694##                                                                   Compound No.                                                                          ##STR695##     R.sub.1                                                                          R.sub.2    Physical data                            __________________________________________________________________________    653                                                                                   ##STR696##     Et Et                                                  654                                                                                   ##STR697##     Et                                                                                ##STR698##                                                                              mp 75-76° C.                      655                                                                                   ##STR699##     i-Pr                                                                              ##STR700##                                                                              mp 96-97° C.                      656                                                                                   ##STR701##     i-Pr                                                                              ##STR702##                                                                              mp 109-111° C.                    657                                                                                   ##STR703##     i-Pr                                                                              ##STR704##                                         658                                                                                   ##STR705##     i-Pr                                                                              ##STR706##                                                                              mp 104-105° C.                    659                                                                                   ##STR707##     i-Pr                                                                              ##STR708##                                                                              mp 99-101° C.                     660                                                                                   ##STR709##     Et Et         n.sub.D.sup.18 1.5511                    661                                                                                   ##STR710##     i-Pr                                                                              ##STR711##                                                                              mp 90-92° C.                      662                                                                                   ##STR712##     i-Pr                                                                              ##STR713##                                                                              mp 91-92° C.                      663                                                                                   ##STR714##     i-Pr                                                                              ##STR715##                                         664                                                                                   ##STR716##     i-Pr                                                                              ##STR717##                                         665                                                                                   ##STR718##     i-Pr                                                                              ##STR719##                                                                              mp 87-89° C.                      666                                                                                   ##STR720##     i-Pr                                                                              ##STR721##                                                                              mp 93-94° C.                      667                                                                                   ##STR722##     i-Pr                                                                              ##STR723##                                         668                                                                                   ##STR724##     i-Pr                                                                              ##STR725##                                         669                                                                                   ##STR726##     i-Pr                                                                              ##STR727##                                         670                                                                                   ##STR728##     i-Pr                                                                              ##STR729##                                         671                                                                                   ##STR730##     i-Pr                                                                              ##STR731##                                         672                                                                                   ##STR732##     i-Pr                                                                              ##STR733##                                         673                                                                                   ##STR734##     i-Pr                                                                              ##STR735##                                         674                                                                                   ##STR736##     i-Pr                                                                              ##STR737##                                         675                                                                                   ##STR738##     i-Pr                                                                              ##STR739##                                                                              mp 160-161° C.                    676                                                                                   ##STR740##     i-Pr                                                                              ##STR741##                                         677                                                                                   ##STR742##     i-Pr                                                                              ##STR743##                                                                              mp 164-165° C.                    678                                                                                   ##STR744##     i-Pr                                                                              ##STR745##                                                                              mp 128-130° C.                    679                                                                                   ##STR746##     i-Pr                                                                              ##STR747##                                         680                                                                                   ##STR748##     i-Pr                                                                              ##STR749##                                         681                                                                                   ##STR750##     i-Pr                                                                              ##STR751##                                         682                                                                                   ##STR752##     i-Pr                                                                              ##STR753##                                         683                                                                                   ##STR754##     i-Pr                                                                              ##STR755##                                         684                                                                                   ##STR756##     i-Pr                                                                              ##STR757##                                         __________________________________________________________________________

Next, a process for the production of a1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (I) according to the first aspect of this invention will beexplained.

Generally, the compound of the general formula (I) may be prepared by aprocess which comprises reacting a 1-substituted-1,2,4-triazol-5-onederivative of the general formula (II) given below with a carbamoylchloride of the general formula (III) given below. ##STR758##

In the above reaction equation, A means an unsubstituted or substitutedphenyl group of the following formula: ##STR759## where X and n have thesame meanings as defined above, or A means 1-naphtyl group,5,6,7,8-tetrahydro-1-naphtyl group or an aralkyl group of the formula:##STR760## where X, n, R₃ and k have the same meanings as defined aboveand R₁ and R₂ have the same meanings as defined above (the samedefinitions as above are used likewise hereinafter).

The reaction in the above-mentioned process can be achieved bycontacting the 1-substituted-1,2,4-triazol-5-one derivative of thegeneral formula (II) with the carbamoyl chloride of the general formula(III) in an organic solvent in the presence of a dehydrochlorinatingagent.

As the dehydrochlorinating agent used in the above-mentioned reaction,there may be mentioned a base, for example, an organic tertiary aminesuch as triethylamine, tributylamine, diethylisopropylamine,4-dimethylaminopyridine and pyridine, or an alkali metal carbonate suchas sodium carbonate or potassium carbonate, or an alkali metal hydroxidesuch as sodium hydroxide and potassium hydroxide. Preferred bases arepyridine and potassium carbonate. Preferably, said base is used in anamount of about one equivalent proportion when sodium carbonate is used.However, when pyridine is used as the base, pyridine is used in anexcess amount since it acts also as a solvent.

As the solvent usable in the reaction, there may be mentioned anaromatic hydrocarbon such as benzene, toluene and xylene; a halogenatedhydrocarbon such as dichloromethane, chloroform, carbon tetrachloride,dichloroethane, trichloroethane and tetrachloroethane; a nitrile such asacetonitrile and propionitrile; an ester such as ethyl acetate and ethylpropionate; an ether such as diethyl ether and tetrahydrofuran; a ketonesuch as acetone and methyl ethyl ketone; and pyridine and so on. Amixture of these solvents may also be used. Acetone and pyridine arepreferred.

The reaction is carried out usually at a temperature ranging from roomtemperature to 150° C., but preferably at 20 to 80° C. The reaction iscompleted usually in a time of between 30 minutes and 24 hours,depending upon the reaction temperature and reactants used.

The compound of the general formula (I) which is a target reactionproduct may be recovered from the resulting reaction solution bysubjecting the reaction solution to usual post-treatments. For example,said target compound can be harvested by adding water to the reactionsolution, washing the solution with water and then distillating off thesolvent. The resulting target product may further be purified by anoperation such as column chromatography or recrystallization, ifnecessary.

Examples of the production of the compound of the general formula (I) ofthis invention according to the above-mentioned process are illustratedwith reference to Examples 1 to 9 given hereinafter.

By the way, the 1-substituted-1,2,4-triazol-5-one derivatives of thegeneral formula (II) used as the starting material in theabove-mentioned process are either a novel compound or a known compound.For example, they can easily be synthesized according to the method asdescribed in the "SYNTHETIC COMMUNICATIONS", Vol.16 (2), pages 163 to167 (1986). The production of them are illustrated with reference toReferential Production Examples 1 to 4 given hereinafter.

Also, the carbamoyl chlorides of the general formula (III) used as thereactant in the process above are well known in the field of an organicchemistry and can easily be synthesized according to the method asdescribed in the "Chemische Berichte", Vol.88, page 301 (1955).

Furthermore, a herbicidal composition according to the second aspect ofthis invention will now be described concretely.

The compound of the general formula (I) according to this invention hasan excellent herbicidal activity as shown in Test Examples hereinafterand can be used as a herbicide for combatting weeds. The compound ofthis invention can be used as a selective herbicide since the compoundmay exhibit a selective herbicidal activity between weeds and cropplants as shown below.

As unwanted grass weeds, there may be mentioned water foxtail(Alopecurus), wild oat (Avena), rescue grass (Bromus), iris sedge(Cyperus), southern crabgrass (Digitaria), barnyard grass (Echinochloa),water chestnut (Eleocharis), goose grass (Eleusine), pickerelweed(Monochoria), fall panicum (Panicum), dallisgrass (Paspalum), timothy(Phleum), annual bluegrass (Poa), arrowhead (Sagittaria), Japanesebulrush (Scirpus), green foxtail (Setaria), Johnson glass (Sorghum) andthe like.

As unwanted broad-leaved weeds, there may be mentioned vervetleaf(Abutilon), livid amaranth (Amaranthus), ragweed (Ambrosia), hairybeggarticks (Bidens), lamb's quarters (Chenopodium), cleaver (Galium),bindweed (Ipomoea), common false pimpernel (Lindernia), smartweed(Persicaria), common purslane (Portulaca), Indian toothcup (Rotala),common chickweed (Stellaria), violet (Viola), heartleaf cocklebur(Xanthium) and the like.

As useful cultivative crops plants of Gramineae grown in the field wherethe compound of this invention may be applied, there may be mentionedbarley (Hordeum), rice (Oryzae), sugar cane (Saccharum), wheat(Triticum), maize (Zea) and the like. As broad-leaved crops, there maybe mentioned peanut (Arachis), sugar beet (Beta), rape (Brassica), soybean (Glycine), cotton (Gossypium), tomato (Lyncopersicon) and the like.

It is needless to say that the use of the compound of the generalformula (I) as herbicide is not limited to the above-mentioned unwantedweeds and the fields for the above-mentioned crop plants.

In the preparation of the herbicidal composition according to the secondaspect of this invention, the1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivative according tothe first aspect of this invention may be formulated into a compositionwherein said compound is incorporated as an active ingredient incombination with a carrier. When formulating into such a herbicidalcomposition, it is possible to formulate into various appropriate formsusually usable in the field of pesticide, for example, granules, finegranules, wettable powder, granular wettable powder, emulsifiableconcentrate, aqueous solution, flowable preparation, tablet, powder andso on, by mixing the compound of the general formula (I) as the activeingredient with a carrier or diluent, and, if desired, also with atleast one of additives and auxiliary agents, in a conventional manner.

Also, it is possible to use the compound of this invention inassociation with other pesticides such as fungicide, insecticide,herbicide, acaricide, plant growth regulating agent, fertilizer, soilconditioner and the like. Particularly, by using the compound of thisinvention in association with other herbicide, it is possible not onlyto reduce the applied amount of the compound of this invention and togain a labour-saving, but also it can be expected to obtain a spreadingof the herbicidal spectrum due to the cooperative action of both theagents, as well as enhanced herbicidal effect due to synergistic action.Then, it is also possible to combine the compound of this invention withtwo or more known herbicides.

The carrier which may be used in the above-mentioned formulation of theherbicidal composition includes such ones which are conventionallyemployed in the preparations of agricultural utility, and which may beeither solid or liquid. The available carrier is not limited to specificone. For example, the solid carrier may include mineral powders such askaolin, bentonite, clay, montmorilonite, talc, diatomaceous earth, mica,vermiculite, quartz, calcium carbonate, phosphorite, white carbon,slaked lime, silicious sand, ammonium sulfate and urea; vegetablepowders such as soya bean flour, wheat flour, wood meal, tobaco powder,starch and crystalline cellulose; macromolecular compounds such aspetroleum resin, polyvinyl chloride and ketone resin; alumina,silicates, sugar polymers, high-dispersible silicic acid and waxes.

The usable liquid carrier may include water; alcohols such as methanol,ethanol, n-propanol, iso-propanol, butanol, ethylene glycol and benzylalcohol; aromatic hydrocarbons such as toluene, benzene, xylene,ethylbenzene and methylnaphthalene; halogenated hydrocarbons such aschloroform, carbon tetrachloride, dichloromethane, chloroethylene,monochlorobenzene, trichlorofluoromethane and dichlorofluoromethane;ethers such as ethyl ether, ethylene oxide, dioxane and tetrahydrofuran;ketones such as acetone, methyl ethyl ketone, cyclohexanone, methylisobutyl ketone and isophorone; esters such as ethyl acetate, butylacetate, ethylene glycol acetate and amyl acetate; acid amides such asdimethylformamide and dimethylacetamide; nitriles such as acetonitrile,propionitrile and acrylonitrile; sulfoxides such as dimethylsulfoxide;alcohol ethers such as ethylene glycol monomethylether and ethyleneglycol monoethylether; aliphatic and cycloaliphatic hydrocarbons such asn-hexane and cyclohexane; industrial gasoline such as petroleum etherand solvent naphtha; and petroleum fractions such as paraffins, keroseneand gas oil.

When the herbicidal composition is prepared in the form of emulsifiableconcentrate, wettable powder, flowable preparation and the like, variouskinds of surface active agents may be added in the composition for thepurpose of emulsification, dispersion, solubilization, wetting, foaming,lubrication, spreading or the like. These surface active agents may be asurface active agent of non-ionic type such as polyoxyethylenealkylethers, polyoxyethylene alkylesters and polyoxyethylene sorbitanalkylesters; a surface active agent of anionic type such as alkylbenzenesulfonates, alkylsulfosuccinate, alkyl sulphates, polyoxyethylenealkylsulfate and aryl sulfonate; and a surface active agent of cationictype such as alkylamines (laurylamine, stearyl trimethyl ammoniumchloride and the like) and polyoxyethylene alkylamine; as well as asurface active agent of amphoteric type such as carboxylic acid ofbetaine type and salts of sulfuric esters. Of course, the surface activeagents usable for this invention are not limited to these surface activeagents as exemplified above.

In addition to the additives mentioned above, the herbicidal compositionmay further contain a variety of adjuvants, for example, polyvinylalcohol (PVA), carboxymethylcellulose (CMC), gum arabic, polyvinylacetate, sodium alginate, gelatine, casein and traganth gum.

When the herbicidal composition of the second aspect of this inventionis formulated in any various forms as exemplified above, the compound ofthe general formula (I) according to this invention may be incorporatedin the composition in an amount of 0.001% to 95% by weight, preferably,0.01% to 75% by weight of the composition. Unless otherwise statedhereinafter, the % value is given on the weight basis hereinafter. Forexample, the content of the compound of the formula (I) may usually be0.01% to 10% in the composition in the form of powder; or 1% to 75% inthe composition in the form of a wettable powder, flowable preparation,solution or emulsifiable concentrate; or 0.01% to 5% in the compositionin the form of powder, driftless powder or fine powder.

The herbicidal composition so prepared, for example, in the form ofgranules and flowable preparation, may be applied by scattering thecomposition as such on the surface of soil or in the soil or in aquaticmedium so that the amount of the active ingredient applied is in a rangeof 0.3 g to 300 g per 10 ares of a farm field. When the herbicidalcomposition is prepared in the form of a wettable powder andemulsifiable concentrate, the herbicidal composition of this form isfirst diluted with water or an appropriate organic solvent and theso-diluted liquid preparation is then applied so that the amount of theactive ingredient applied is in a range of 0.3 g to 300 g per 10 ares ofa farm field.

In addition, it has been found that a number of the exemplifiedcompounds among the compounds of the general formula (I) according tothe first aspect of this invention can completely kill weeds of thepaddy field and weeds of farm field at a rate of kill of weed of 100%,even when they are applied at a rate as low as 3 g to 30 g per 10 aresof the field and thus they can exhibit an excellent herbicidal activity.

Hereinafter, several examples of the production of the compound of thegeneral formula (I) according to this invention will be described withreference to the following Examples and Referential Production Examples.

EXAMPLE 1

Production of1-(2-chlorophenyl)-4-(N-isopropyl-N-2,4-difluorophenylcarbamoyl)-1,2,4-triazol-5-one(Compound No.35 of Table 1a)

To a solution of 1-(2-chlorophenyl)-1,2,4-triazol-5-one (2.0 g) inacetonitrile (50 ml) was added potassium carbonate (1.7 g). Theresulting mixture was stirred for 30 minutes at room temperature, andN-isopropyl-N-2,4-difluorophenylcarbamoyl chloride (3.0 g) was added tothe mixture, followed by stirring the resulting mixture for one hour at80° C. The resulting reaction solution was then filtered to remove theinorganic salt as formed therefrom. Thereafter, the solvent wasdistilled out from the filtrate under reduced pressure. The residueobtained was dissolved in 80 ml of toluene, and the resulting solutionwas washed with water and then dried over anhydrous sodium sulfate.Thereafter, the solvent was distilled off from the solution. The residueso obtained was purified by silica gel chromatography to give 3.2 g ofthe titled target compound (at a yield of 80%). Melting point of 146 to148° C.

EXAMPLE 2

Production of1-(2-chlorophenyl)-4-(N-isopropyl-N-4-fluorophenylcarbamoyl)-1,2,4-triazol-5-one(Compound No.38 of Table 1a)

To a solution of 1-(2-chlorophenyl)-1,2,4-triazol-5-one (2.0 g) inpyridine (50 ml) was added N-isopropyl-N-fluorophenylcarbamoyl chloride(2.6 g). The resulting mixture was left to stand for 20 hours at roomtemperature. Pyridine was distilled off from the resulting reactionsolution under reduced pressure. The resulting residue was dissolved in80 ml of toluene, and the solution obtained was washed with 1N aqueoushydrochloric acid and then with water and dried over anhydrous sodiumsulfate. The dried solution was distilled to remove the solventtherefrom, and the resulting residue was purified by silica gelchromatography to give 2.9 g of the titled target compound (at a yieldof 77%). Melting point of 118 to 120° C.

EXAMPLE 3

Production of1-phenyl-4-(N-isopropyl-N-phenyl-carbamoyl)-1,2,4-triazol-5-one(Compound No.1 of Table 1a)

To a solution of 1-phenyl-1,2,4-triazol-5-one (1.6 g) in pyridine (50ml)was added N-isopropyl-N-phenylcarbamoyl chloride (2.4 g). The resultingmixture was left to stand for 20 hours at room temperature. Pyridine wasdistilled off from the resulting reaction solution under reducedpressure. The resulting residue was dissolved in 80 ml of toluene, andthe solution obtained was washed with 1N aqueous hydrochloric acid andthen with water and dried over anhydrous sodium sulfate. The solvent wasdistilled off from the solution and the resulting residue was purifiedby silica gel chromatography to give 2.4 g of the titled target compound(at a yield of 77%). Melting point of 144 to 145° C.

EXAMPLE 4

Production of1-(2-chlorophenyl)-4-(N-ethyl-N-2,4-difluorophenylcarbamoyl)-1,2,4-triazol-5-one(Compound No.26 of Table 1a)

To a solution of 1-(2-chlorophenyl)-1,2,4-triazol-5-one (2.0 g) inpyridine (50ml) was added N-ethyl-N-2,4-difluorophenylcarbamoyl chloride(2.8 g). The resulting mixture was left to stand for 20 hours at roomtemperature. Pyridine was distilled off from the resulting reactionsolution under reduced pressure. The resulting residue was dissolved in80 ml of toluene, and the solution obtained was washed with 1N aqueoushydrochloric acid and then with water and dried over anhydrous sodiumsulfate. The solvent was distilled off from the solution and theresulting residue was purified by silica gel chromatography to give 3.0g of the titled target compound (at a yield of 79%). Melting point of110 to 111° C.

EXAMPLE 5

Production of1-(2-chlorophenyl)-4-(N-ethyl-N-cyclohexylcarbamoyl)-1,2,4-triazol-5-one(Compound No.66 of Table 1a)

To a solution of 1-(2-chlorophenyl)-1,2,4-triazol-5-one (2.0 g) inpyridine (50 ml) was added N-ethyl-N-cyclohexylcarbamoyl chloride (2.0g). The resulting mixture was left to stand for 20 hours at roomtemperature. Pyridine was distilled off from the resulting reactionsolution under reduced pressure. The resulting residue was dissolved in80 ml of toluene, and the solution obtained was washed with 1N aqueoushydrochloric acid and then with water and dried over anhydrous sodiumsulfate. The solvent was distilled off from the solution and theresulting residue was purified by silica gel chromatography to give 3.0g of the titled compound (at a yield of 84%, melting point of 105 to106° C.).

EXAMPLE 6

Production of1-(2-methylphenyl)-4-(N-isopropyl-N-2,4-difluorophenylcarbamoyl) -1,2,4-triazol-5-one (Compound No.331 of Table 1a)

To a solution of 1-(2-methylphenyl)-1,2,4-triazol-5-one (1.89) inpyridine (50 ml) was added N-isopropyl-N-2,4-difluorophenylcarbamoylchloride (3.0 g). The resulting mixture was left to stand for 20 hoursat room temperature. Pyridine was distilled off from the resultingreaction solution under reduced pressure. The resulting residue wasdissolved in 80 ml of toluene, and the solution obtained was washed with1N aqueous hydrochloric acid and then with water and dried overanhydrous sodium sulfate. The solvent was distilled off from thesolution and the resulting residue was purified by silica gelchromatography to give 3.1 g of the titled target compound (at a yieldof 81%). Melting point of 106 to 107° C.

EXAMPLE 7

Production of1-(2,4-dichlorophenyl)-4-(N-isopropyl-N-2,4-difluorophenylcarbamoyl)-1,2,4-triazol-5-one(Compound No.231 of Table 1a)

To a solution of 1-(2,4-dichlorophenyl)-1,2,4-triazol-5-one (2.3 g) inpyridine (50ml) was added N-isopropyl-N-2,4-difluorophenylcarbamoylchloride (3.0 g). The resulting mixture was left to stand for 20 hoursat room temperature. Pyridine was distilled off from the resultingreaction solution under reduced pressure. The resulting residue wasdissolved in 80 ml of toluene, and the solution obtained was washed with1N aqueous hydrochloric acid and then with water and dried overanhydrous sodium sulfate. The solvent was distilled off and theresulting residue was purified by silica gel chromatography to give 3.1g of the titled target compound (at a yield of 71%). Melting point of129 to 131° C.

EXAMPLE 8

Production of1-(2-chloro-α-methylbenzyl)-4-(N-isopropyl-N-2,4-difluorophenylcarbamoyl)-1,2,4-triazol-5-one(Compound No.675 of Table 1c)

To a solution of 1-(2-chloro-α-methylbenzyl)-1,2,4-triazol-5-one (1.0 g)in acetonitrile (30 ml) was added potassium carbonate (0.8 g) . Theresulting mixture was stirred for 30 minutes at room temperature andthen N-isopropyl-N-2,4-difluorophenylcarbamoyl chloride (1.3 g) wasadded thereto. The resulting mixture was stirred for one hour at 80° C.The resulting reaction solution was then filtered to remove theinorganic salt as formed therefrom. Thereafter, the solvent was removedfrom the filtrate by distillation under reduced pressure. The residueobtained was dissolved in 50 ml of toluene, and the resulting solutionwas washed with water and then dried over anhydrous sodium sulfate.Thereafter, the solvent was distilled off from the solution. The residueso obtained was purified by silica gel chromatography to give 1.3 g ofthe titled target compound (at a yield of 68%). Melting point of 160 to161° C.

EXAMPLE 9

Production of1-benzyl-4-(N-isopropyl-N-2,4-difluorophenylcarbamoyl)-1,2,4-triazol-5-one(Compound No.656 of Table 1c)

1-benzyl-1,2,4-triazol-5-one (1.3 g) andN-isopropyl-N-2,4-difluorophenylcarbamoyl chloride (2.3 g) were added topyridine (30 ml). The resulting mixture was stirred for one hour at roomtemperature and then left to stand over night. To the resulting reactionsolution were added toluene (150 ml) and water (150 ml). Then, theresulting mixture was separated into two phases. The toluene layerobtained was further washed with 1N aqueous hydrochloric acid and with asaturated aqueous sodium chloride solution and subsequently dried overanhydrous sodium sulfate. The dried toluene solution was distilled underreduced pressure to remove the solvent, and the resulting residue waspurified by silica gel chromatography to give 1.5 g of the titled targetcompound (at a yield of 54%). Melting point of 109 to 111° C.

REFERENTIAL PRODUCTION EXAMPLE 1

Preparation of 1-(2-chlorophenyl)-1,2,4-triazol-5-one

25 g of 2-chlorophenylhydrazine hydrochloride was dissolved in 230 ml ofwater. To the resulting solution, 29 g of an aqueous solution of 40% ofglyoxylic acid was added dropwise under ice-cooling. The resultingmixture was stirred for 2 hours at a temperature of 10 to 20° C. and thepowder thus deposited was recovered by filtration under suction and thenwashed with water. The resulting powder was dried under reduced pressurein a desiccator to obtain 27.2 g of a brown powder. 27.2 g of the powderso obtained was suspended in 400 ml of toluene, and 14 g oftriethylamine was added dropwise to the resulting suspension, followedby adding dropwise 37.8 g of diphenylphosphoryl azide to it. Theresulting mixture was stirred under heating for 4 hours at 70 to 80° C.and further for 2 hours at 100° C. The resulting reaction solution wasallowed to cool and then extracted with 760 ml of 1N aqueous potassiumhydroxide solution under cooling with ice-water. The alkaline aqueouslayer obtained as the extract solution was made acidic by adding 160 gof a concentrated hydrochloric acid portionwise. The crystals thusdeposited were separated by filtration and washed with water. Theresulting crystals were dissolved in a mixed solvent of toluene andethanol, and the solution obtained was subjected to azeotropicdistillation under reduced pressure to remove water therefrom. Thecrystals so obtained were recrystallised from ethyl acetate to obtain19.1 g of the titled target compound (at a yield of 70%). Melting pointof 155 to 156° C.

REFERENTIAL PRODUCTION EXAMPLE 2

Preparation of 1-phenyl-1,2,4-triazol-5-one

12 g of phenylhydrazine hydrochloride was dissolved in 100 ml of water.To the resulting solution was added 15.3 g of an aqueous solution of 40%of glyoxylic acid dropwise under ice-cooling. The resulting mixture wasstirred for 2 hours at a temperature of 10 to 20° C. The powder thusdeposited was separated by filtration under suction and then washed withwater. The resulting powder was dried under reduced pressure in adesiccator to obtain 12.9 g of a brown powder. 12.9 g of the powder thusobtained was suspended in 250 ml of toluene, and to the resultingsuspension was added dropwise 7.9 g of triethylamine, followed by addingdropwise 21.7 g of diphenylphosphoryl azide. The resulting reactionmixture was stirred under heating for 2 hours at 70 to 80° C. andfurther for 1 hour at 100° C. The resulting reaction solution wasallowed to cool and then extracted with 400 ml of 2N aqueous sodiumhydroxide solution under cooling with ice-water. The alkaline aqueouslayer obtained as the extract solution was made acidic by adding 90 g ofa concentrated hydrochloric acid portionwise. The crystals thusdeposited were recovered by filtration and washed with water. Theresulting crystals were dissolved in a mixed solvent of toluene andethanol, and the solution obtained was subjected to azeotropicdistillation under reduced pressure to remove water therefrom. Thecrystals so obtained were recrystallised from ethyl acetate to obtain9.1 g of the titled target compound (at a yield of 68%) Melting point of182 to 183° C.

REFERENTIAL PRODUCTION EXAMPLE 3

Preparation of 1-(2-chloro-α-methylbenzyl)-1,2,4-triazol-5-one

4.5 g of 2-chloro-α-methylhydrazine hydrochloride was dissolved in 100ml of water. To the resulting solution, 4.1 g of an aqueous solution of40% of glyoxylic acid was added dropwise under ice-cooling. Theresulting mixture was stirred for 2 hours at a temperature of 10 to 20°C. and then the powder thus deposited was recovered by filtration undersuction and then washed with water. The resulting powder was dried underreduced pressure in a desiccator to obtain 4.7 g of a brown powder. 4.7g of the powder obtained was suspended in 100 ml of toluene, and to theresulting suspension was then added dropwise 2.1 g of triethylamine,followed by adding dropwise 5.7 g of diphenylphosphoryl azide. Theresulting reaction mixture was stirred under heating for 1 hour at 70 to80° C. and further for 1 hour at 100° C. The resulting reaction solutionwas allowed to cool and then extracted with 100 ml of 2N aqueouspotassium hydroxide solution under cooling with ice-water. The alkalineaqueous layer so obtained as the extract solution was made acidic byadding 25 g of a concentrated hydrochloric acid portionwise. Thecrystals thus deposited were separated by filtration and washed withwater. The resulting crystals were dissolved in a mixed solvent oftoluene and ethanol, and the solution obtained was subjected toazeotropic distillation under reduced pressure to remove watertherefrom. The crystals so obtained were recrystallised from ethylacetate to obtain 3.0 g of the titled target compound (at a yield of65%). Melting point of 141 to 144° C.

REFERENTIAL PRODUCTION EXAMPLE 4

Preparation of 1-benzyl-1,2,4-triazol-5-one

16.2 g of benzylhydrazine dihydrochloride was dissolved in 300 ml ofwater. To the resulting solution, 15.4 g of an aqueous solution of 40%of glyoxylic acid was added dropwise under cooling with ice-water. Theresulting mixture was stirred for 1 hour at a temperature of 10 to 20°C. and the powder thus deposited was recovered by filtration and washedwith water. The resulting powder was dried under reduced pressure in adesiccator to obtain 9.9 g of a brown powder. 9.0 g of the powderobtained was suspended in 250 ml of toluene, and to the resultingsuspension was added dropwise 5.1 g of triethylamine, followed by addingdropwise 13.9 g of diphenylphosphoryl azide. The resulting reactionmixture was stirred under heating for 1 hour at 70 to 80° C. and furtherfor 1 hour at 100° C. The resulting reaction solution was allowed tocool and then extracted with 300 ml of 2N aqueous sodium hydroxidesolution under cooling with ice-water. The resulting alkaline aqueouslayer was made acidic by adding portionwise 60 g of a concentratedhydrochloric acid and then extracted with 150 ml of ethyl acetate. Theresulting ethyl acetate layer (the extract solution) was washed with asaturated aqueous sodium chloride solution and then dried over anhydroussodium sulfate. The resulting dried solution was distilled under reducedpressure to remove the solvent. The resulting residue was purified bysilica gel chromatography to obtain 4.7 g of the titled target compound(at a yield of 53%) Melting point of 147 to 149° C.

Another representative particular examples of the1-substituted-1,2,4-triazole which are represented by the generalformulas (IIa), (IIb) and (IIc) given below and which were produced inthe same manner as in the above Referential Production Examples 1 to 4are shown in the following Tables 2-1, 2-2 and 2-3.

                  TABLE 2-1                                                       ______________________________________                                        General formula (IIa):                                                         ##STR761##                                                                   X.sub.n              mp.                                                      ______________________________________                                        H                    182-183° C.                                       2-Cl                 155-156° C.                                       4-Cl                 256-257° C.                                       2-F                  164-165° C.                                       3-F                  166-168° C.                                       4-F                  231-232° C.                                       2-Br                 150-151° C.                                       2,3-Cl.sub.2         194-195° C.                                       2,4-Cl.sub.2         188-189° C.                                       2,5-Cl.sub.2         183-185° C.                                       2,6-Cl.sub.2         243-244° C.                                       2-F,4-Cl             208-209° C.                                       2,4-F.sub.2          231-232° C.                                       2-Me                 148-149° C.                                       3-Me                 183-184° C.                                       4-Me                 211-212° C.                                       2-Et                 149-151° C.                                       2-n-Pr               113-114° C.                                       2-i-Pr               153-154° C.                                       2,3-(Me).sub.2       190-192° C.                                       2,4-(Me).sub.2       146-148° C.                                       2,5-(Me).sub.2       135-137° C.                                       2,6-(Me).sub.2       167-168° C.                                       2-Me,6-Et            143-144° C.                                       2-MeO                127-128° C.                                       4-MeO                180-181° C.                                       2-MeS                136-138° C.                                       2-CN                 169-171° C.                                       4-CF.sub.3           258-260° C.                                       2-Me,3-Cl            197-198° C.                                       2-Me,4-Cl            192-193° C.                                       2-Me,5-Cl            187-188° C.                                       2-Me,6-Cl            198-199° C.                                       4-Me,2-Cl            159-161° C.                                       2-NO.sub.2           181-182° C.                                       2-NHCOMe             262-263° C.                                       2-NHCOCF.sub.3       156-158° C.                                       2,4,6-Cl.sub.3       268-269° C.                                       ______________________________________                                    

                  TABLE 2-2                                                       ______________________________________                                        General formula (IIb):                                                         ##STR762##                                                                   where A.sup.a means                                                            ##STR763##                                                                   or                                                                             ##STR764##                                                                   A.sup.a         mp.                                                           ______________________________________                                         ##STR765##     mp 188-189° C.                                          ##STR766##     mp 191-192° C.                                         ______________________________________                                    

                  TABLE 2-3                                                       ______________________________________                                        General formula (IIc):                                                         ##STR767##                                                                   Xn          R.sub.3   k     mp.                                               ______________________________________                                        H           H         1     147-149° C.                                2-Cl        H         1     162-164° C.                                2-Me        H         1     166-168° C.                                2-Cl        Me        1     141-144° C.                                2-Me        Me        1     156-158° C.                                ______________________________________                                    

Furthermore, various and exemplary formulations of the herbicidalcomposition comprising the compound of the above general formula (I)according to this invention are now illustrated with reference to thefollowing Examples 10 to 15, to which this invention is not limited inany way. It is feasible to incorporate in the exemplified formulationsoptional proportions of another different additives and also toformulate the exemplified formulations in any desired form. Compound No.shown in the following Examples indicates the compound number listed inTables 1a, 1b and 1c given hereinbefore. In these Examples, "part" or"parts" are all given on the weight basis.

EXAMPLE 10 (Granules)

    ______________________________________                                        Compound No. 1    1          part                                             Calcium ligninsulfonate                                                                         1          part                                             Lauryl sulfate    1          part                                             Bentonite         30         parts                                            Talc              67         parts                                            ______________________________________                                    

The resultant mixture of the above ingredients was mixed with 15 partsof water and then kneaded in a kneader. The kneaded mixture wasgranulated in an extruder-type granulating machine, and the granulesobtained were dried in a drying apparatus of fluidization-type. In thisway, the granules containing 1% by weight of the active ingredient wereprepared.

EXAMPLE 11 (Flowable preparation)

    ______________________________________                                        Compound No. 35       20.0      parts                                         Di-2-ethylhexyl sulfosuccinate sodium salt                                                          2.0       parts                                         Polyoxyethylene nonylphenyl ether                                                                   2.0       parts                                         Propylene glycol      5.0       parts                                         Anti-foaming agent    0.5       parts                                         Water                 70.5      parts                                         ______________________________________                                    

The above ingredients were evenly mixed with each other and ground in awet-type ball mill. In this way, a flowable preparation containing 20%by weight of the active ingredient was prepared.

EXAMPLE 12 (Dry flowable preparation)

    ______________________________________                                        Compound No. 331         75     parts                                         Isovan No. 1 (an anionic surfactant, a commercial                                                      10     parts                                         product of Kurare Isoprene Chemical Co., Japan)                               Vanilex N (an anionic surfactant, a commercial                                                         5      parts                                         product of Sanyo Kokusaku Pulp Co., Japan)                                    White carbon             5      parts                                         Clay                     5      parts                                         ______________________________________                                    

The above ingredients were evenly mixed with each other and finelyground in a grinding and mixing machine. In this way, a dry flowablepreparation (a granular wettable powder) containing 75% by weight of theactive ingredient was prepared.

EXAMPLE 13 (Wettable powder)

    ______________________________________                                        Compound No. 231     15       parts                                           White carbon         15       parts                                           Calcium ligninsulfonate                                                                            3        parts                                           Polyoxyethylene nonylphenyl ether                                                                  2        parts                                           Diatomaceous earth   5        parts                                           Clay                 60       parts                                           ______________________________________                                    

The above ingredients were evenly mixed with each other in a grindingand mixing machine. In this way, a wettable powder containing 15% byweight of the active ingredient was prepared.

EXAMPLE 14 (Emulsifiable concentrate)

    ______________________________________                                        Compound No. 8            20 parts                                            Sorpor 700H (an emulsifier, a commercial product                                                        20 parts                                            of Toho Chemical Industry Co., Japan)                                         Xylene                    60 parts                                            ______________________________________                                    

The above ingredients were mixed with each other. In this way, anemulsifiable concentrate containing 20% by weight of the activeingredient was prepared.

EXAMPLE 15 (Powder)

    ______________________________________                                        Compound No. 481                                                                              0.5          parts                                            White carbon    0.5          parts                                            Calcium stearate                                                                              0.5          parts                                            Clay            50.0         parts                                            Talc            48.5         parts                                            ______________________________________                                    

The above ingredients were ground and mixed homogeneously with eachother. In this way, a powder containing 0.5% by weight of the activeingredient was obtained.

It will be needless to say that all the herbicidal compositionscomprising the compound of the above general formula (I) according tothis invention may be formulated into different types of herbicidalfromulations, respectively, similarly to the formulation Examples shownin above.

Now, the following Test Examples 1 to 4 are shown in order todemonstrate the herbicidal effects of the compounds of the formula (I)according to this invention.

Test Example 1

Tests of the herbicidal effects of the compound on early watergrass andtests of phyto-toxicity of the compound to aquatic rice plant (theherbicidal treatment on pre-emergence of unwanted weeds and theherbicidal treatment conducted one day after the transplantation ofaquatic rice plant).

Each of pots having a top surface area of 1/5000 ares was filled with asoil of the irrigated rice field. The soil in each pot was added with avolume of water and with a complex fertilizer (N:P:K=17:17:17) and thenwas puddled. In the surface layer of the watered soil were sownuniformly seeds of early watergrass to depth of 1 cm in the surfacelayer of the soil. In the soil in each pot, there were transplantedseedlings of aquatic rice plants (variety:Nihonbare) of 2.5-leavedstage. Each pot was then irrigated with water and the depth of theirrigating water on the soil surface was kept at about 3 cm. Each potwas subsequently controlled under the condition of glass greenhouse.

A diluted solution of a wettable powder was prepared by diluting withwater to a predetermined concentration of the active ingredient such awettable powder which had been formulated similarly to the procedure ofExample 13 above. One day after the transplantation of the aquatic riceplant, the diluted solution prepared as above was dropwise added at apredetermined rate to the irrigating water in the pot to conduct theherbicidal treatment. 28 Days after the herbicidal treatments, theherbicidal effects of the tested compound on early watergrass andphyto-toxicity of the tested compound to aquatic rice plant wereassessed, and the rate (percentages) of kill of the weeds was calculatedaccording to the under-mentioned calculation equation. The test resultsobtained are shown in Table 3 below.

Rate (%) of kill of weeds=[1-(a/b)]×100 wherein a represents the dryweight (g) of weeds in treated plot and b represents the dry weight (g)of weeds in untreated plot.

Besides, phyto-toxicity of the tested compound to aquatic rice plant wasassessed according to the following gradings of evaluation.

    ______________________________________                                        Gradings of evaluation for the                                                                     Observed degrees of                                      Phyto-toxicity to rice plant                                                                       damage of rice plant                                     ______________________________________                                        5                    Complete kill                                            4                    Great damage                                             3                    Medium damage                                            2                    Low damage                                               1                    Very low damage                                          0                    Null                                                     ______________________________________                                    

As a reference chemical, comparative compound A indicated hereinafterwas used, and a wettable powder containing said comparative compound Awas prepared in accordance with the procedure of Example 13 above. As acomparative test, the resultant diluted solution of the wettable powderwas tested in the same manner as in the above tests for the compounds ofthis invention. The test results obtained are shown in Table 3 below.Compound No. shown in the following Table indicates the compound numberlisted in Tables 1a, 1b and 1c given hereinbefore.

                  TABLE 3                                                         ______________________________________                                                   Application rate                                                              of the active                                                      Test Compound                                                                            ingredient  Rate (%) of                                            No.        (g/10 ares) kill of weeds                                                                            Phyto-toxicity                              ______________________________________                                         1         15          100        0                                            4         4           100        0                                            8         4           100        0                                            25        4           100        0                                            26        4           100        0                                            27        4           100        0                                            28        4           100        0                                            29        4           100        0                                            30        4           100        0                                            31        4           100        0                                            32        4           100        0                                            33        4           100        0                                            34        4           100        0                                            35        1           100        0                                            38        1           100        0                                            42        4           100        0                                            65        15          100        0                                            66        4           100        0                                            72        15          100        0                                            73        15          100        0                                            74        15          100        0                                            75        15          100        0                                            76        15          100        0                                            85        2           100        0                                            88        4           100        0                                           135        15          100        0                                           165        4           100        0                                           166        1           100        0                                           169        15          100        0                                           170        4           100        0                                           181        2           100        0                                           184        4           100        0                                           200        2           100        0                                           221        1           100        0                                           222        1           100        0                                           231        2           100        0                                           234        2           100        0                                           269        2           100        0                                           270        2           100        0                                           281        2           100        0                                           284        2           100        0                                           318        4           100        0                                           320        15          100        0                                           322        2           100        0                                           324        2           100        0                                           331        1           100        0                                           334        2           100        0                                           381        4           100        0                                           384        4           100        0                                           431        2           100        0                                           434        2           100        0                                           481        1           100        0                                           484        1           100        0                                           518        2           100        0                                           520        15          100        0                                           521        4           100        0                                           522        4           100        0                                           531        4           100        0                                           534        4           100        0                                           576        2           100        0                                           577        2           100        0                                           581        4           100        0                                           582        4           100        0                                           586        4           100        0                                           587        4           100        0                                           591        2           100        0                                           592        2           100        0                                           596        1           100        0                                           597        1           100        0                                           631        2           100        0                                           632        2           100        0                                           633        15          100        9                                           634        15          100        0                                           635        4           100        0                                           636        4           100        0                                           637        15          100        0                                           638        15          100        0                                           639        2           100        0                                           640        4           100        0                                           650        4           100        0                                           656        15          100        0                                           658        15          100        0                                           662        4           100        0                                           665        4           100        0                                           666        4           100        0                                           675        4           100        0                                           678        15          100        0                                           Comparative                                                                              100          60        3                                           Compound A                                                                    ______________________________________                                    

Comparative Compound A used in this test Example was a tetrazolinonederivative of the formula ##STR768## namely1-phenyl-4-(N-isopropyl-N-phenylcarbamoyl)-tetrazolin-5-one which isdisclosed in Japanese patent application Kokai No. 62-12767.(Comparative Compound A was also used similarly in the following TestExamples 2 to 4 below.)

Test Example 2

Tests of the herbicidal effects on early watergrass (Herbicidaltreatments of unwanted weeds during the growing period of weed

Each of pots having a top surface area of 1/5000 ares was filled with asoil of the irrigated rice field. The soil in each pot was added with avolume of water and with a complex fertilizer (N:P:K=17:17:17) and thenwas puddled. In the surface layer of the watered soil were sownuniformly seeds of early watergrass to depth of 1 cm in the surfacelayer of the soil.

Each pot was then irrigated with water and the depth of the irrigatingwater on the soil surface was kept at 3 cm. Each pot was subsequentlycontrolled under the condition of glass greenhouse.

A diluted solution of a wettable powder was prepared by diluting withwater to a predetermined concentration of the active ingredient such awettable powder which had been formulated similarly to the procedure ofExample 13 above. At the 1.5-leaved stage of the early watergrassgrowing in each pot, the diluted solution prepared as above was dropwiseadded at predetermined rate to the irrigating water in the pot toconduct the herbicidal treatment.

21 Days after the herbicidal treatments, the herbicidal effects on earlywatergrass were investigated, and the rate (percentages) of kill of theweeds was assessed on the same gradings as that in Test Example 1. Awettable powder containing as a reference chemical comparative compoundA was prepared in accordance with the procedure of Example 13 above. Fora comparative test, the resultant diluted solution of said wettablepowder was tested in the same manner as in the above tests for thecompounds of this invention. The test results obtained are shown inTable 4 below. Compound No. shown in the following Table indicates thecompound number listed in Tables 1a, 1b and 1c hereinbefore.

                  TABLE 4                                                         ______________________________________                                                     Application rate of                                              Test Compound                                                                              the active ingredient                                                                      Rate (%) of kill                                    No.          (g/10 ares)  of weeds                                            ______________________________________                                         1           30           100                                                  4           8            100                                                  8           8            100                                                  25          8            100                                                  26          8            100                                                  27          8            100                                                  28          8            100                                                  29          8            100                                                  30          8            100                                                  31          8            100                                                  32          8            100                                                  33          8            100                                                  34          8            100                                                  35          2            100                                                  38          2            100                                                  42          8            100                                                  65          30           100                                                  66          8            100                                                  72          30           100                                                  73          30           100                                                  74          30           100                                                  75          30           100                                                  76          30           100                                                  85          4            100                                                  88          4            100                                                 135          30           100                                                 165          8            100                                                 166          2            100                                                 169          30           100                                                 170          8            100                                                 181          4            100                                                 184          4            100                                                 200          4            100                                                 221          2            100                                                 222          2            100                                                 231          4            100                                                 234          4            100                                                 269          4            100                                                 270          4            100                                                 281          4            100                                                 284          4            100                                                 318          8            100                                                 320          30           100                                                 322          4            100                                                 324          4            100                                                 331          2            100                                                 334          2            100                                                 381          8            100                                                 384          8            100                                                 431          4            100                                                 434          4            100                                                 481          2            100                                                 484          2            100                                                 518          2            100                                                 520          30           100                                                 521          15           100                                                 522          8            100                                                 531          4            100                                                 534          8            100                                                 576          4            100                                                 577          8            100                                                 581          15           100                                                 582          8            100                                                 586          8            100                                                 587          15           100                                                 591          8            100                                                 592          8            100                                                 596          4            100                                                 597          4            100                                                 631          8            100                                                 632          8            100                                                 633          30           100                                                 634          30           100                                                 635          15           100                                                 636          15           100                                                 637          30           100                                                 638          30           100                                                 639          8            100                                                 640          30           100                                                 650          30           100                                                 656          30           100                                                 658          30           100                                                 662          30           100                                                 665          15           100                                                 666          15           100                                                 675          15           100                                                 678          30           100                                                 Comparative  100           50                                                 Compound A                                                                    ______________________________________                                    

Test Example 3

Tests of the herbicidal effects on weeds (common false pimpernel,Monochoria, Japanese bulrush) predominant in irrigated field of aquaticrice plant

Each of pots having a top surface area of 1/5000 ares was filled with asoil of the rice field. The soil in each pot was added with a volume ofwater and with a complex fertilizer (N:P:K=17:17:17) and then puddled.30 Seeds of weeds, that is, common false-pimpernel, Monochoria andJapanese bulrush were sown in separate pots, respectively, to a depth of2 cm in the soil of these pots. Immediately after the sowing of seeds,each pot was irrigated with water and the depth of the irrigating wateron the soil surface was kept at 2 cm. Each pot was subsequently managedin the green house. A wettable powder as formulated similarly to theprocedure of Example 13 above was diluted with water to a predeterminedconcentration of the active ingredient, and the resultant dilutedpreparation of the herbicidal compound so prepared was dropwise added ata predetermimed rate to the pots at one day after the weed seed sowing.

21 Days after the herbicidal treatments made by the above application ofthe herbicidal compound, the rate (%) of kill of the weeds was assessedand evaluated in the same manner as in Test Example 1. Further, awettable powder containing Comparative Compound A as a referencechemical was prepared in accordance with the procedure of Example 13above and was tested in the same manner as the compound of thisinvention. The results obtained are shown in Table 5 below. Compound No.shown in the following Table indicates the compound number listed inTables 1a-1c hereinbefore.

                  TABLE 5                                                         ______________________________________                                                             Rate (%) of kill of weeds                                         Application rate                                                                          predominant in irrigated field                           Test     of the active                                                                             of aquatic rice plant                                    Compound ingredient  False            Japanese                                No.      (g/10 ares) pimpernel                                                                              Monochoria                                                                            bulrush                                 ______________________________________                                        1        15          100      95      95                                      4        4           100      100     100                                     8        4           100      100     100                                     25       4           100      100     100                                     26       4           100      100     100                                     27       4           100      100     100                                     28       4           100      100     100                                     29       4           100      100     100                                     30       4           100      100     100                                     31       4           100      100     100                                     32       4           100      100     100                                     33       4           100      100     100                                     34       4           100      100     100                                     35       2           100      100     100                                     38       2           100      100     100                                     42       4           100      100     100                                     65       15          100      90      90                                      66       4           100      100     100                                     72       15          100      90      95                                      73       15          100      90      95                                      74       15          100      90      95                                      75       15          95       100     100                                     76       15          90       90      100                                     85       2           100      100     100                                     88       4           100      100     100                                     135      15          90       90      90                                      165      4           100      90      90                                      166      2           100      100     100                                     169      15          90       90      100                                     170      4           100      100     90                                      181      2           100      100     100                                     184      4           100      100     100                                     200      2           100      100     100                                     221      2           100      95      100                                     222      2           100      100     100                                     231      2           100      100     100                                     234      2           100      100     100                                     269      4           100      100     100                                     270      4           100      100     100                                     281      2           100      100     100                                     284      2           100      100     100                                     318      4           95       90      100                                     320      15          100      90      95                                      322      2           100      100     100                                     324      2           100      100     100                                     331      2           100      100     100                                     334      2           100      100     100                                     381      4           100      100     100                                     384      4           100      100     100                                     431      4           100      100     100                                     434      4           100      100     100                                     481      2           100      100     100                                     484      2           100      100     100                                     518      4           100      100     100                                     520      15          90       95      90                                      521      4           100      95      100                                     522      4           100      100     95                                      531      4           100      100     100                                     534      4           100      100     100                                     576      4           100      100     100                                     577      4           100      100     100                                     581      4           100      100     100                                     582      4           100      95      100                                     586      4           100      100     100                                     587      4           95       100     95                                      591      4           100      100     100                                     592      4           100      100     100                                     596      2           100      100     100                                     597      2           100      100     100                                     631      4           100      100     100                                     632      4           95       100     90                                      633      15          95       95      90                                      634      15          95       95      95                                      635      4           100      90      90                                      636      4           100      95      90                                      637      15          90       90      90                                      638      15          90       90      90                                      639      4           100      100     100                                     640      4           100      100     100                                     650      4           100      100     100                                     656      15          95       95      95                                      658      15          95       100     95                                      662      4           100      100     100                                     665      4           100      100     100                                     666      4           100      100     100                                     675      4           100      100     100                                     678      15          95       95      100                                     Comparative                                                                            100         70       70      40                                      Compound A                                                                    ______________________________________                                    

Test Example 4

Test of herbicidal effects on weeds predominant in farm-field(non-irrigated) and tests of phyto-toxicity to crop plants

1) Tests of herbicidal effects on weeds in farm-field

Each of biscuit pots having a top surface area of 1/5000 ares was filledwith a farm-field soil (Alluvium loam). In the soil top layer of up tothe 1 cm depth in each pot, the soil was evenly mixed with 50 seeds ofeach sort of weeds chosen from southern crabgrass, green foxtail, vervetleaf, livid amaranth and tufted knotweed. The soil top surfacecontaining the sown seeds was pressed lightly in each pot. Anemulsifiable concentrate as formulated similarly to the procedure ofExample 14 above was diluted with water to prepare a diluted emulsionpreparation of the herbicidal compound. 2 Days after the seed sowing,the diluted emulsion preparation was applied by spraying to the soilsurface in each pot at such a rate that the amount of the emulsionpreparation applied was 100 liters per 10 ares. This was equivalent tothat the amount of the active ingredient applied was at a rate of 50 gof the active ingredient per 10 ares.

30 Days after the treatments with the emulsion preparation, theherbicidal effects were evaluated in terms of the rate (%) of kill ofweeds which was calculated according to the same gradings as shown inTest Example 1 above.

2) Tests of phyto-toxicity to crop plants

Each of biscuit pots having a top surface area of 1/10,000 ares wasfilled with a farm-field soil (Alluvium loam), and in the soil of theseseparete pots were sown seeds of various crop plants (namely, 5 seeds ofsoybean, 5 seeds of maize, 10 seeds of sugar beet, 10 seeds of rape, 5seeds of cotton, 10 seeds of wheat and 10 seeds of barley). The soilsurface layer containing the sown seeds was pressed lightly in each pot.An emulsifiable concentrate as formulated similarly to Example 14 abovewas diluted with water to prepare a diluted emulsion preparation. Oneday after the seed sowing, the diluted emulsion preparation was appliedby spraying to the soil surface in each pot at such a rate that theamount of the emulsion preparation applied was 100 liters per 10 ares.This was equivalent to that the amount of the active ingredient appliedwas at a rate of 50 g per 10 ares.

30 Days after the treatments with the emulsion preparation, the degreeof phyto-toxicity to various crop plants was assessed according to thegradings of evaluation same as those given in Test Example 1 above.

The results obtained are shown in Table 6 below. Compound No. shown inthe following Table indicates the compound number listed in Tables 1a-1chereinbefore.

In both the tests (1) of the herbicidal effects and the tests (2) of thephyto-toxicity, a comparative emulsifiable concentrate containing saidComparative Compound A as a reference chemical was prepared inaccordance with the procedure of Example 14 above and was tested in thesame manner as the compound of this invention.

                                      TABLE 6                                     __________________________________________________________________________    Test  Rate (%) of kill of weeds in farm-field                                 Compound                                                                            Southern                                                                           Green                                                                             Vervet                                                                            Livid                                                                              Tufted                                                                             Phyto-toxicity to crop plants                    No.   crabgrass                                                                          foxtail                                                                           leaf                                                                              amaranth                                                                           knotweed                                                                           Soy bean                                                                           Maize                                                                             sugar beet                                                                         Rape                                                                             Wheat                                                                             Barley                                                                            Cotton                  __________________________________________________________________________    1     90   100 90  90   90   0    0   0    0  0   0   0                       4     100  100 90  90   95   1    1   0    0  0   0   0                       8     100  100 90  90   90   0    1   0    0  0   0   0                       25    100  100 90  90   90   0    1   1    0  0   0   0                       26    100  100 90  90   90   1    0   0    0  0   0   0                       27    100  100 90  90   90   0    0   0    0  0   0   0                       28    100  100 90  90   90   0    0   0    0  0   0   0                       29    100  100 90  90   90   0    0   1    0  0   0   0                       30    100  100 95  95   90   0    1   0    0  0   0   0                       31    100  100 95  90   90   0    1   1    0  0   1   0                       32    100  100 90  90   90   0    1   1    0  0   0   1                       33    100  100 95  90   90   0    1   0    0  0   0   0                       34    100  100 95  90   90   0    1   1    0  0   0   0                       35    100  100 100 95   90   0    0   0    0  0   0   0                       38    100  100 100 100  95   0    0   1    0  0   0   0                       42    100  100 95  90   90   0    0   0    0  0   0   1                       65    95   100 90  90   90   0    1   1    0  0   0   0                       66    100  100 90  90   90   0    1   0    1  0   0   0                       72    90   95  90  90   90   1    0   1    0  0   0   0                       73    95   100 90  90   90   1    0   0    0  1   0   0                       74    95   100 90  90   90   0    0   1    0  0   0   0                       75    95   100 90  90   95   0    0   1    0  0   0   0                       76    95   95  100 100  95   0    0   0    1  0   1   0                       85    100  100 95  90   90   0    0   0    0  0   0   0                       88    100  100 95  90   90   0    0   1    0  0   0   0                       135   95   95  95  100  90   0    0   0    0  1   0   0                       165   100  100 100 95   90   0    1   0    0  1   0   0                       166   100  100 90  90   95   0    1   0    0  1   1   0                       169   100  100 90  95   95   0    1   0    0  0   0   0                       170   100  100 90  95   95   0    0   0    0  1   1   0                       181   100  100 95  90   90   0    0   0    0  0   0   0                       184   100  100 100 90   90   0    1   0    0  0   0   0                       200   100  100 100 95   90   0    1   0    1  0   1   0                       221   100  100 100 90   90   0    1   1    0  1   1   0                       222   100  100 100 95   95   0    1   0    0  1   1   0                       231   100  100 95  90   90   1    0   0    0  1   0   0                       234   100  100 100 90   90   0    0   0    0  0   0   0                       269   100  100 95  95   95   0    0   1    0  1   1   0                       270   100  100 95  90   90   0    0   1    0  0   1   1                       281   100  100 100 90   90   0    1   0    0  0   0   0                       284   100  100 95  90   90   0    0   0    0  0   0   0                       318   100  100 90  90   90   0    1   0    1  0   0   0                       320   90   90  90  90   90   0    1   0    0  1   1   0                       322   100  100 100 90   90   1    1   0    0  1   0   0                       324   100  100 90  90   95   1    1   0    0  1   0   0                       331   100  100 95  90   90   0    0   1    0  0   0   0                       334   100  100 95  90   90   0    1   0    1  0   0   0                       381   100  100 95  90   90   0    0   0    0  0   0   0                       384   100  100 95  90   90   0    1   0    1  0   0   0                       431   100  100 90  90   90   0    0   1    0  0   0   0                       434   100  100 95  90   90   0    0   0    0  1   0   0                       481   100  100 95  90   90   0    1   0    1  0   0   0                       484   100  100 100 95   90   1    1   0    0  0   0   0                       518   100  95  95  90   95   0    1   1    0  1   1   0                       520   95   95  90  95   95   1    1   0    0  1   0   1                       521   100  100 100 100  100  0    1   0    1  0   1   0                       522   100  100 95  95   95   0    1   1    0  1   1   0                       531   100  100 90  90   90   0    0   0    0  0   0   0                       534   100  100 90  90   90   0    0   0    0  0   0   0                       576   100  100 95  90   90   0    0   0    1  1   0   0                       577   100  100 95  90   90   0    0   0    1  1   0   0                       581   100  100 90  90   90   0    0   0    1  0   1   1                       582   100  100 90  90   95   0    1   1    0  1   0   0                       586   100  100 90  90   100  0    1   1    0  1   0   0                       587   100  100 95  95   100  1    0   0    0  1   0   0                       591   100  100 100 95   100  0    1   0    0  0   1   0                       592   100  100 95  100  100  0    1   0    0  0   0   0                       596   100  100 90  100  100  1    0   0    0  0   0   0                       597   100  100 95  90   90   0    1   0    0  0   1   0                       631   100  100 90  90   90   0    1   0    0  0   1   0                       632   100  100 90  95   90   0    0   0    0  1   1   0                       633   100  90  90  90   100  1    0   0    0  1   1   1                       634   100  100 90  90   95   0    1   1    0  0   0   0                       635   100  100 95  95   100  1    0   0    0  0   1   0                       636   100  100 95  95   95   0    0   0    1  1   0   0                       637   100  90  90  90   90   0    1   0    0  1   0   0                       638   100  95  90  90   90   0    1   1    0  1   0   0                       639   100  100 95  95   100  0    0   1    1  0   0   0                       640   100  100 95  95   100  0    0   1    1  0   0   0                       650   100  100 90  90   95   0    0   0    1  0   0   0                       656   100  90  90  90   95   0    1   1    0  1   0   0                       658   100  95  90  90   90   0    0   1    1  0   0   0                       662   100  100 90  95   95   0    0   1    0  0   0   0                       665   100  100 90  95   95   1    0   1    0  1   0   0                       666   100  100 90  90   100  0    1   1    0  1   0   0                       675   100  100 95  95   100  0    0   0    1  1   1   0                       678   100  95  90  95   100  0    0   0    0  1   0   0                       Comparative                                                                         70   70  70  60   40   3    2   3    3  0   0   0                       Compound                                                                      __________________________________________________________________________

Industrial Availability

As described in the above, the new, herbicidal1-substituted-4-carbamoyl-1,2,4-triazol-5-one derivatives according tothis invention have an excellent herbicidal activity and can achieve acomplete kill of various sorts of weeds in both the irrigated field ofaqatic rice plant and the farm-fields even at a lower application rateof the compound, and also they have excellent selectivity between usefulcrop plants and unwanted weeds. Accordingly, the new compound of thisinvention is very useful as a selective herbicide.

What is claimed is:
 1. A 1-substituted-4-carbamoyl-1,2,4-triazol-5-onederivative represented by the general formula (I) ##STR769## wherein:(i) A is an unsubstituted or substituted phenyl group represented by theformula ##STR770## in which X may be the same or different and is ahalogen atom, a lower alkyl group, a lower haloalkyl group, a loweralkoxy group, a lower haloalkoxy group, cyano group, nitro group,methylthio group, methylsulfinyl group, methylsulfonyl group, phenoxygroup, acetylamino group or trifluoroacetylamino group, and n is 0 or aninteger of 1 to 5, or(ii) A is 1-naphthyl group of the formula##STR771## or 5,6,7,8-tetrahydro-1-naphthyl group of the formula##STR772## (iii) A is an unsubstituted or substituted benzyl group orphenethyl group represented by the formula ##STR773## in which X and nhave the same meanings as defined above, R₃ is hydrogen atom or methylgroup and k denotes an integer of 1 to 2;R₁ is a lower alkyl group, alower alkenyl group, a lower alkynyl group or a lower cycloalkyl group;and R₂ is a lower alkyl group, a lower cycloalkyl group or anunsubstituted or substituted phenyl group having the formula ##STR774##in which m is 0 or an integer of 1 to 5 and Y may be the same ordifferent and is a halogen atom, a lower alkyl group, a lower haloalkylgroup, a lower alkoxy group, a lower haloalkoxy group or cyano group; orR₂ is a benzyl group of which benzene ring may be substituted with ahalogen atom; or R₂ is an unsubstituted or substituted pyridyl grouphaving the formula ##STR775## in which Z is hydrogen atom or chlorineatom.
 2. A derivative as claimed in claim 1, wherein the derivative ofthe general formula (I) is a 1-phenyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative represented by the generalformula (Ia) ##STR776## wherein: X has the same meaning as defined inclaim 1, wherein X may be the same or different and is a halogen atom, alower alkyl group, a lower haloalkyl group, a lower alkoxy group, alower haloalkoxy group, cyano group, nitro group, methylthio group,methylsulfinyl group, methylsulfonyl group, phenoxy group, acetylaminogroup or trifluoroacetylamino group;n is 0 or an integer of 1 to 5; andR₁ and R₂ have the same meanings as defined in claim 1, wherein R₁ is alower alkyl group, a lower alkenyl group, a lower alkynyl group or alower cycloalkyl group, and R₂ is a lower alkyl group, a lowercycloalkyl group or an unsubstituted or substituted phenyl group havingthe formula ##STR777## in which m is 0 or an integer of 1 to 5 and Y maybe the same or different and is a halogen atom, a lower alkyl group, alower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group orcyano group; or R₂ is a benzyl group of which benzene ring may besubstituted with a halogen atom; or R₂ is an unsubstituted orsubstituted pyridyl group having the formula ##STR778## in which Z ishydrogen atom or chlorine atom.
 3. A derivative as claimed in claim 2,wherein the derivative of the general formula (Ia) is a1-phenyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-one derivativerepresented by the general formula (Ia-1) ##STR779## where R_(1a) is alower alkyl group, R_(2a) is a mono-halo- or di-halo-substituted phenylgroup, X^(a) is a halogen atom, a lower alkyl group or a lower haloalkylgroup, and n is 0 or an integer of 1 to
 2. 4. A derivative as claimed inclaim 2, wherein the derivative of the general formula (Ia) is a1-phenyl-4-(N, N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative represented by the general formula (Ia-1-1) ##STR780## wherei-Pr means isopropyl group, R_(2a) is a mono-halo- ordi-halo-substituted phenyl group, X^(a) is a halogen atom, a lower alkylgroup or a lower haloalkyl group, and n is 0 or an integer of 1 to
 2. 5.A derivative as claimed in claim 4, wherein the derivative of thegeneral formula (Ia-1-1) is a 1-phenyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative represented by the generalformula (Ia-1-2) ##STR781## where i-Pr means isopropyl group, T ishydrogen atom or fluorine atom, X^(b) may be the same or different andis chlorine atom.
 6. A derivative as claimed in claim 5, wherein thederivative of the general formula (Ia-1-2)is:1-phenyl-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-phenyl-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one1-(2-chlorophenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-chlorophenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(3-chlorophenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(3-chlorophenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-fluorophenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-fluorophenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2,4-difluorophenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2,4-difluorophenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-fluoro-4-chlorophenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-fluoro-4-chlorophenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoy)-1,2,4-triazol-5-one,1-(2-methylphenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-methylphenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2,3-dimethylphenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2,3-dimethylphenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-chloro-4-methylphenyl)-4-(N-isopropyl-N-4-fluorophenyl-carbamoyl)-1,2,4-triazol-5-one,1-(2-chloro-4-methylphenyl)-4-(N-isopropyl-N-2,4-difluorophenyl-carbamoyl)-1,2,4-triazol-5-one.7. A derivative as claimed in claim 2, wherein the derivative of thegeneral formula (Ia) is a 1-phenyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative represented by the generalformula (Ia-2) ##STR782## where X and n have the same meanings asdefined in claim 2, R_(1b) is a lower alkyl group, and R_(2b) is a lowercycloalkyl group.
 8. A derivative as claimed in claim 7, which is a1-phenyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-one derivativeof the general formula (Ia-2) where X is chlorine atom, fluorine atom,methyl group, ethyl group, trifluoromethyl group or trifluoromethyloxygroup, n is 0 or an integer of 1 to 2, R_(1b) is methyl group, ethylgroup, n-propyl group or isopropyl group, and R_(2b) is cyclopropylgroup, cyclopentyl group or cyclohexyl group.
 9. A derivative as claimedin claim 1, wherein the derivative of the general formula (I) is a1-naphthyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative represented by the general formula (Ib) ##STR783## in whichA^(a) is 1-naphthyl group of the formula ##STR784## or5,6,7,8-tetrahydro-1-naphthyl group of the formula ##STR785## R₁ and R₂have the same meanings as defined in claim 1, wherein R₁ is a loweralkyl group, a lower alkenyl group, a lower alkynyl group or a lowercycloalkyl group, and R₂ is a lower alkyl group, a lower cycloalkylgroup or an unsubstituted or substituted phenyl group having the formula##STR786## in which m is 0 or an integer of 1 to 5 and Y may be the sameor different and is a halogen atom, a lower alkyl group, a lowerhaloalkyl group, a lower alkoxy group, a lower haloalkoxy group or cyanogroup; or R₂ is a benzyl group of which benzene ring may be substitutedwith a halogen atom; or R₂ is an unsubstituted or substituted pyridylgroup having the formula ##STR787## in which Z is hydrogen atom orchlorine atom.
 10. A derivative as claimed in claim 9, which is a1-naphthyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative represented by the general formula (Ib) where R₁ is a loweralkyl group and R₂ is a mono-halo- or di-halo-substituted phenyl group.11. A derivative as claimed in claim 1, wherein the derivative of thegeneral formula (I) is a 1-aralkyl-4-(N,N-di-substitutedcarbamoyl)-1,2,4-triazol-5-one derivative represented by the generalformula (Ic) ##STR788## in which: X has the same meaning as defined inclaim 1, wherein X may be the same or different and is a halogen atom, alower alkyl group, a lower haloalkyl group, a lower alkoxy group, alower haloalkoxy group, cyano group, nitro group, methylthio group,methylsulfinyl group, methylsulfonyl group, phenoxy group, acetylaminogroup or trifluoroacetylamino group;n is 0 or an integer of 1 to 5; R₁and R₂ have the same meanings as defined in claim 1, wherein R₁ is alower alkyl group, a lower alkenyl group, a lower alkynyl group or alower cycloalkyl group, and R₂ is a lower alkyl group, a lowercycloalkyl group or an unsubstituted or substituted phenyl group havingthe formula ##STR789## in which m is 0 or an integer of 1 to 5 and Y maybe the same or different and is a halogen atom, a lower alkyl group, alower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group orcyano group; or R₂ is a benzyl group of which benzene ring may besubstituted with a halogen atom; or R₂ is an unsubstituted orsubstituted pyridyl group having the formula ##STR790## in which Z ishydrogen atom or chlorine atom; R₃ is hydrogen atom or methyl group; andk is an integer of 1 or
 2. 12. A derivative as claimed in claim 11,wherein the derivative of the general formula (Ic) is a1-aralkyl-4-(N,N-di-substituted carbamoyl)-1,2,⁴ -triazol-5-onederivative represented by the general formula (Ic-1) ##STR791## whereR_(1a) is a lower alkyl group, R_(2a) is a mono-halo- ordi-halo-substituted phenyl group, X^(a) is a halogen atom, a lower alkylgroup or a lower haloalkyl group, n is 0 or an integer of 1 to 2 and kis an integer of 1 or
 2. 13. A derivative as claimed in claim 12,wherein the derivative of the general formula (Ic-1) is a1-aralkyl-4-(N,N-di-substituted carbamoyl)-1,2,4-triazol-5-onederivative represented by the general formula (Ic-1-1) ##STR792## inwhich i-Pr means isopropyl group, T is hydrogen atom or fluorine atom,X^(b) may be the same or different and is chlorine atom, bromine atom,fluorine atom, methyl group, ethyl group or trifluoromethyl group, n is0 or an integer of 1 to 2, R₃ is hydrogen atom or methyl group and k isan integer of 1 or
 2. 14. A herbicidal composition comprising as anactive ingredient a 1-substituted-4-carbamoyl-1,2,4-triazol-5-onederivative represented by the general formula (I) ##STR793## wherein A,R₁ and R₂ have the same meanings as defined in claim
 1. 15. A herbicidalcomposition as claimed in claim 14, which comprises as an activeingredient a 1-phenyl-4-carbamoyl-1,2,4-triazol-5-one derivative of thegeneral formula (Ia).
 16. A herbicidal composition as claimed in claim14, which comprises as an active ingredient a1-naphthyl-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (Ib).
 17. A herbicidal composition as claimed in claim 14, whichcomprises as an active ingredient a1-aralkyl-4-carbamoyl-1,2,4-triazol-5-one derivative of the generalformula (Ic).